1. Benzene to 'Halo'benzene by Asch

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310 reactions in Reaxys

2016-05-12 15h:08m:40s (EST)

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Rx-ID: 848944 View in Reaxys 1/310 Yield 100 %

Conditions & References With carbon dioxide, bromine, Time= 2h, T= 40 °C , p= 187519Torr , Supercritical conditions, Green chemistry Delgado-Abad, Thais; Martnez-Ferrer, Jaime; Reig-Lpez, Javier; Mello, Rossella; Acerete, Rafael; Asensio, Gregorio; Gonzlez-Nez, Mara Elena; RSC Advances; vol. 4; nb. 92; (2014); p. 51016 - 51021 View in Reaxys

96 %

With Pb3O4, trifluoroacetic acid, potassium bromide, T= 20 °C , reagents ratio, Product distribution Makhon'kov, D. I.; Cheprakov, A. V.; Rodkin, M. A.; Serguchev, Yu. A.; Davydova, V. G.; Beletskaya, I. P.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 11; (1987); p. 2424 - 2426; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 11; (1987); p. 2609 - 2611 View in Reaxys

92.5 %

With tetrabutylammomium bromide, hydrogen peroxide, bromine in water, Time= 8h, T= 65 °C , different reagents, Product distribution Dakka, Jihad; Sasson, Yoel; Journal of the Chemical Society, Chemical Communications; nb. 19; (1987); p. 1421 1422 View in Reaxys

92 %

2.6 Typical procedure for the bromination General procedure: NBS (1.0 mmol) and catalyst 1 (0.1 or 1 mol percent Au based on the substrate) were weighted into a 10 mL sealed vessel, and then DCE (2 mL) and the substrate (1.0 mmol) were added. The reaction was stirred at the required temperature for the specified time. After reaction, the catalyst was removed with a magnet, and the solution was concentrated under reduced pressure and purified by column chromatography. With N-Bromosuccinimide in 1,2-DICHLOROETHANE, Time= 11h, T= 80 °C , Sealed tube Li, Bai; Gao, Linfeng; Bian, Fengling; Yu, Wei; Tetrahedron Letters; vol. 54; nb. 9; (2013); p. 1063 - 1066 View in Reaxys

91 %

With N-Bromosuccinimide, sulfuric acid, trifluoroacetic acid, Time= 2h, T= 25 °C , Bromination Duan, Jianxin; Zhang, Lian Hao; Dolbier Jr., William R.; Synlett; nb. 8; (1999); p. 1245 - 1246 View in Reaxys

89 %

With sulfuric acid, bromine, mercury(II) oxide in tetrachloromethane, Time= 1h, Heating, other deactivated aromatic rings, Product distribution Khan, Shabbir Afzal; Munawar, M. A.; Siddiq, M.; Journal of Organic Chemistry; vol. 53; nb. 8; (1988); p. 1799 1800 View in Reaxys

89 %

With sulfuric acid, bromine, mercury(II) oxide in tetrachloromethane, Time= 1h, Heating Khan, Shabbir Afzal; Munawar, M. A.; Siddiq, M.; Journal of Organic Chemistry; vol. 53; nb. 8; (1988); p. 1799 1800 View in Reaxys

88 %

With Oxonereg;, sodium bromide in water, Time= 1.5h, T= 20 °C Firouzabadi; Iranpoor; Kazemi; Canadian Journal of Chemistry; vol. 87; nb. 12; (2009); p. 1675 - 1681 View in Reaxys

86 %

With PyHBrCl2, iron(III) chloride in dichloromethane, Time= 1h, T= 20 °C Muathen, Hussni A.; Synthesis; nb. 2; (2002); p. 169 - 171 View in Reaxys

85 %

With bromine, dinitrogen tetraoxide, carbon, iron nitrate (III), Time= 2.5h, T= 20 °C

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Firouzabadi; Iranpoor; Shiri; Tetrahedron Letters; vol. 44; nb. 49; (2003); p. 8781 - 8785 View in Reaxys 85 %

With ammonium nitrate, N-Bromosuccinimide in acetonitrile, Time= 8h Tanemura, Kiyoshi; Suzuki, Tsuneo; Nishida, Yoko; Satsumabayashi, Koko; Horaguchi, Takaaki; Chemistry Letters; vol. 32; nb. 10; (2003); p. 932 - 933 View in Reaxys

82 %

With hydrochlorid acid, sodium hypochlorite, sodium bromide in water, Time= 8h, T= 29.85 °C , Product distribution, Further Variations: Temperatures, Reagents Sadygov; Alimardanov; Chalabiev; Russian Journal of Organic Chemistry; vol. 41; nb. 11; (2005); p. 1631 - 1636 View in Reaxys

82 %

With cerium(III) chloride heptahydrate, hydrogen peroxide, sodium bromide in water, Time= 4.5h, T= 20 °C , regioselective reaction Firouzabadi, Habib; Iranpoor, Nasser; Kazemi, Somayeh; Ghaderi, Arash; Garzan, Atefeh; Advanced Synthesis and Catalysis; vol. 351; nb. 11-12; (2009); p. 1925 - 1932 View in Reaxys

81.3 %

3 :29.10 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with water condenser. To it, 5 equivalents (57 ml, 0.73 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70° C. under stirring. A solution of 15.5 ml (35percent) hydrochloric acid (0.15 mol) was added to the hot reaction mixture over 10 hours. The mixture was stirred for another 30 h at 70° C. and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 18.6 g or 81.3percent of clear and colorless liquid bromo benzene having boiling point 154-156° C. With hydrochlorid acid, hypobromous acid, sodium lauryl sulfate in water, Time= 40h, T= 70 °C , Product distribution / selectivity Patent; Bedekar, Ashutosh Vasant; Ghosh, Kumar Pushpito; Adimurthy, Subbarayyappa; Ramachandraiah, Gadde; US2005/137431; (2005); (A1) English View in Reaxys

81.3 %

3 :EXAMPLE 3; 29.10 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with water condenser. To it, 5 equivalents (57 ml, 0.73 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70°C under stirring. A solution of 15.5 ml (35percent) hydrochloric acid (0.15 mol) was added to the hot reaction mixture over 10 hours. The mixture was stirred for another 30 h at 70°C and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 18.6 g or 81.3percent of clear and colorless liquid bromo benzene having boiling point 154-156°C. With hydrochlorid acid, Sodium bromate, sodium lauryl sulfate, sodium bromide in water, Time= 40h, T= 70 °C , Product distribution / selectivity Patent; COUNCIL OF SCIENTIFIC and INDUSTRIAL RESEARCH; WO2005/61423; (2005); (A1) English View in Reaxys

79.6 %

With thallium(III) oxide, potassium bromide in trifluoroacetic acid, Time= 7h, Ambient temperature Gun'kin, I. F.; Russian Journal of General Chemistry; vol. 67; nb. 4; (1997); p. 654 - 655; Zhurnal Obshchei Khimii; vol. 67; nb. 4; (1997); p. 699 - 700 View in Reaxys

79 %

With methanesulfonic acid, monobromoisocynaurate in diethyl ether, Time= 6h, Heating Okada, Yukihiro; Yokozawa, Masanori; Akiba, Miwa; Oishi, Kazuhiko; O-Kawa, Kyoji; Akeboshi, Tomohiro; Kawamura, Yasuo; Inokuma, Seiichi; Nakamura, Yosuke; Nishimura, Jun; Organic and Biomolecular Chemistry; vol. 1; nb. 14; (2003); p. 2506 - 2511

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View in Reaxys 70 %

With DBU-hydrobromide-perbromide, silver sulphate in sulfuric acid, Time= 0.5h, Ambient temperature, HgCl2 instead Ag2SO4; without Ag2SO4; solvent: DMF or aq. DMF; other temp.; other times; same reaction of other aromatic compounds, Product distribution Muathen, Hussni A.; Journal of Organic Chemistry; vol. 57; nb. 9; (1992); p. 2740 - 2741 View in Reaxys

70 %

With DBU-hydrobromide-perbromide, silver sulphate in sulfuric acid, Time= 0.5h, Ambient temperature Muathen, Hussni A.; Journal of Organic Chemistry; vol. 57; nb. 9; (1992); p. 2740 - 2741 View in Reaxys

68 %

With Li2MnO3, bromine, Time= 5h, T= 100 °C , Darkness Nishina, Yuta; Morita, Junya; Ohtani, Bunsho; RSC Advances; vol. 3; nb. 7; (2013); p. 2158 - 2162 View in Reaxys

59.3 %

With [2,5-Me2C6H3SO2N(Br)CH2]2 in tetrachloromethane, Time= 1.5h, T= 77 °C , Bromination Ardeshir, Khazaei; Abbas, Shirdarreh; Synthetic Communications; vol. 29; nb. 23; (1999); p. 4079 - 4085 View in Reaxys

56 %

With pyridine, C36H36N24O12*Br2 in dichloromethane, T= 0 - 75 °C , Reagent/catalyst Reddy; Cavallini; Demets; Silva; New Journal of Chemistry; vol. 38; nb. 6; (2014); p. 2262 - 2264 View in Reaxys

53.5 %

5 :29.10 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with water condenser. To it, 5 equivalents (57 ml, 0.73 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 80° C. under stirring. A solution of 22 ml (70percent) perchloric acid (0.15 mol) was added to the hot reaction mixture over 10 hours. The mixture was stirred for another 30 h at 80° C. and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 10.7 g or 53.5percent of clear and colorless liquid bromo benzene having boiling point 154-156° C. With perchloric acid, hypobromous acid, sodium lauryl sulfate in water, Time= 40h, T= 80 °C , Product distribution / selectivity Patent; Bedekar, Ashutosh Vasant; Ghosh, Kumar Pushpito; Adimurthy, Subbarayyappa; Ramachandraiah, Gadde; US2005/137431; (2005); (A1) English View in Reaxys

53.5 %

4 :EXAMPLE5; 29.10 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with water condenser. To it, 5 equivalents (57 ml, 0.73 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 80°C under stirring. A solution of 22 ml (70percent) perchloric acid (0.15 mol) was added to the hot reaction mixture over 10 hours. The mixture was stirred for another 30 h at 80°C and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 10.7 g or 53.5percent of clear and colorless liquid bromo benzene having boiling point 154- 156°C. With Sodium bromate, perchloric acid, sodium lauryl sulfate, sodium bromide in water, Time= 40h, T= 80 °C , Product distribution / selectivity Patent; COUNCIL OF SCIENTIFIC and INDUSTRIAL RESEARCH; WO2005/61423; (2005); (A1) English View in Reaxys

52.3 - 89.7 %

1; 2; 4 :29.1 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with an water condenser. To it, 5 equivalents (57 ml, 0.73 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70° C. under stirring. A solution of 16.4 ml (50percent) sulfuric acid (0.15 mol) was added to the hot reaction mixture over a period for 10 hours. The mixture

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was stirred for another 30 h at 70° C. and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 20 g or 87.5percent of clear and colorless liquid bromo benzene having boiling point 154-156° C.; 116.4 g of brominating reagent was dissolved in 300 ml water taken in 1000 ml three neck round bottom flask fitted with an water condenser. To it, 5 equivalents (228 ml, 2.92 mol) of benzene per atom of bromine and 0.4 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70° C. under stirring. A solution of 65.6 ml (50percent) sulfuric acid (0.60 mol) was added to the hot reaction mixture over 10 hours. The mixture was stirred for another 30 h at 70° C. and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 82 g or 89.7percent of clear and colorless liquid bromo benzene having boiling point 154-156° C.; 29.10 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with water condenser. To it, 2 equivalents (22.8 ml, 0.292 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70° C. under stirring. A solution of 16.4 ml (50percent) sulfuric acid (0.15 mol) was added to the hot reaction mixture over 8 hours. The mixture was stirred for another 25 h at 80° C. and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 11.9 g or 52.3percent of clear and colorless liquid bromo benzene having boiling point 154-156° C. With sulfuric acid, hypobromous acid, sodium lauryl sulfate in water, Time= 33 - 40h, T= 70 - 80 °C , Product distribution / selectivity Patent; Bedekar, Ashutosh Vasant; Ghosh, Kumar Pushpito; Adimurthy, Subbarayyappa; Ramachandraiah, Gadde; US2005/137431; (2005); (A1) English View in Reaxys 52.3 - 89.7 %

1-2; 4 :EXAMPLE 1; 29.1 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with an water condenser. To it, 5 equivalents (57 ml, 0.73 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70°C under stirring. A solution of 16.4 ml (50percent) sulfuric acid (0.15 mol) was added to the hot reaction mixture over a period for 10 hours. The mixture was stirred for another 30 h at 70°C and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 20 g or 87.5percent of clear and colorless liquid bromo benzene having boiling point 154-156°C.; EXAMPLE 2 116.4 g of brominating reagent was dissolved in 300 ml water taken in 1000 ml three neck round bottom flask fitted with an water condenser. To it, 5 equivalents (228 ml, 2.92 mol) of benzene per atom of bromine and 0.4 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70°C under stirring. A solution of 65.6 ml (50percent) sulfuric acid (0.60 mol) was added to the hot reaction mixture over 10 hours. The mixture was stirred for another 30 h at 70°C and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 82 g or 89.7percent of clear and colorless liquid bromo benzene having boiling point 154-156°C.; EXAMPLE 4 29.10 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with water condenser. To it, 2 equivalents (22.8 ml, 0.292 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70°C under stirring. A solution of 16.4 ml (50percent) sulfuric acid (0. 15 mol) was added to the hot reaction mixture over 8 hours. The mixture was stirred for another 25 h at 80°C and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 11.9 g or 52.3percent of clear and colorless liquid bromo benzene having boiling point 154- 156°C. With Sodium bromate, sulfuric acid, sodium lauryl sulfate, sodium bromide in water, Time= 33 - 40h, T= 70 - 80 °C , Product distribution / selectivity

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Patent; COUNCIL OF SCIENTIFIC and INDUSTRIAL RESEARCH; WO2005/61423; (2005); (A1) English View in Reaxys 40 %

With Ag2SO4, sulfuric acid, tetra-n-butylammonium tribromide, Time= 0.5h, Ambient temperature Chaudhuri, Mihir K.; Khan, Abu T.; Patel, Bhisma K.; Dey, Deepa; Kharmawophlang, Wancydora; Lakshmiprabha; Mandal, Gagan C.; Tetrahedron Letters; vol. 39; nb. 44; (1998); p. 8163 - 8166 View in Reaxys

20 %

With sulfuric acid, hydrogen bromide, hydrogen peroxide in water, Time= 24h, T= 55 °C , Darkness Podgorsek, Ajda; Stavber, Stojan; Zupan, Marko; Iskra, Jernej; Tetrahedron; vol. 65; nb. 22; (2009); p. 4429 4439 View in Reaxys

15 %

With KBrO3 in sulfuric acid, Time= 16h, Ambient temperature Banerjee, Amalendu; Banerjee, Gopal Chandra; Adak, Mohini Mohan; Banerjee, Santa; Samaddar, Haraprasad; Journal of the Indian Chemical Society; vol. 58; (1981); p. 985 - 988 View in Reaxys With manganese triacetate, trifluoroacetic acid, potassium bromide, Time= 15h, Ambient temperature, Co(CH3COO)3, 90percent aq. CF3COOH, 72 h, Product distribution Makhon'kov, D. I.; Cheprakov, A. V.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 22; (1986); p. 609 - 615; Zhurnal Organicheskoi Khimii; vol. 22; nb. 4; (1986); p. 681 - 688 View in Reaxys With bromine, [14C]-Tetramethylammonium bromide in liquid sulphur dioxide, T= -23 °C , var.: in H2O at 25 deg C, NaBr, HClO4, Product distribution, Rate constant Castellonese, Paul; Villa, Pierre; Bulletin de la Societe Chimique de France; vol. 1; nb. 1-2; (1981); p. 42 - 48 View in Reaxys With aluminium trichloride, bromine Leroy; Bulletin de la Societe Chimique de France; vol. <2> 48; (1887); p. 211 View in Reaxys Greene; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 90; (1880); p. 41 View in Reaxys With bromine, beryllium bromide Taboury; Pajeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 202; (1936); p. 328 View in Reaxys With bromine, silver trifluoroacetate Haszeldine; Sharpe; Journal of the Chemical Society; (1952); p. 993,1000 View in Reaxys With bromine, nitric acid Varma; Narayan; ; vol. 4; p. 285; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 489 View in Reaxys With nitrosulfonic acid, bromine, nitric acid Varma; Narayan; ; vol. 4; p. 285; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 489 View in Reaxys With hydrogen bromide, carbon, T= 45 °C , Electrolysis Croco; Lowy; ; vol. 50; p. 318; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 421 View in Reaxys With bromine

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Bruner; Chem. Zentralbl.; vol. 71; nb. II; (1900); p. 257 View in Reaxys Couper; Annales de Chimie (Cachan, France); vol. <3> 52; (1858); p. 309; Justus Liebigs Annalen der Chemie; vol. 104; (1857); p. 225 View in Reaxys With bromine, iodine Michaelis; Graeff; Chemische Berichte; vol. 8; (1875); p. 922 View in Reaxys Schramm; Chemische Berichte; vol. 18; (1885); p. 607 View in Reaxys With aluminium amalgam, bromine Cohen; Dakin; Journal of the Chemical Society; vol. 75; (1899); p. 894 View in Reaxys With bromine, zinc(II) chloride Schiaparelli; Gazzetta Chimica Italiana; vol. 11; (1881); p. 69; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1881); p. 539 View in Reaxys With aluminum tri-bromide, bromine Bruner; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 41; (1902); p. 530 ff View in Reaxys With thallium monochloride, bromine Bruner; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 41; (1902); p. 530 ff View in Reaxys With bromine, phosphorus trichloride Bruner; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 41; (1902); p. 530 ff View in Reaxys With bromine, phosphorus tribromide Bruner; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 41; (1902); p. 530 ff View in Reaxys With bromine, antimony(III) chloride Bruner; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 41; (1902); p. 530 ff View in Reaxys With bromine, antimony(III) bromide Bruner; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 41; (1902); p. 530 ff View in Reaxys With bromine, FeBr2 Bruner; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 41; (1902); p. 530 ff View in Reaxys With pyridine, bromine Chross; Cohen; ; p. 335; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 153 View in Reaxys With KBrO3, sulfuric acid, bromine Krafft; Chemische Berichte; vol. 8; (1875); p. 1045 View in Reaxys

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With bromosulfur, nitric acid Edinger; Goldberg; Chemische Berichte; vol. 33; (1900); p. 2884 View in Reaxys With bromine, iron Gattermann; View in Reaxys With manganese, bromine, unter Feuchtigkeitsausschluss Ducelliez; Gay; Raynaud; Bulletin de la Societe Chimique de France; vol. <4> 15; (1914); p. 738 View in Reaxys Gay; Ducelliez; Raynaud; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p. 1804; Bulletin de la Societe Chimique de France; vol. <4> 15; (1914); p. 737 View in Reaxys With hypobromous acid Stark; Chemische Berichte; vol. 43; (1910); p. 672 View in Reaxys With bromine, nitric acid Datta; Chatterjee; Journal of the American Chemical Society; vol. 38; (1916); p. 2548 View in Reaxys With sulfuric acid, bromine, nitric acid Varma; Narayan; ; vol. 4; p. 285; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 489 View in Reaxys With bromine, silver perchlorate, magnesium oxide Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys With bromine, nitric acid, silver nitrate, unter Ausschluss von Licht Derbyshire; Waters; Journal of the Chemical Society; (1950); p. 573,576 View in Reaxys 97 % Chromat.

With KBrO3, sulfuric acid in water Harrison, J.J.; Pellegrini, J.P.; Selwitz, C.M.; Journal of Organic Chemistry; vol. 46; nb. 10; (1981); p. 2169 - 2171 View in Reaxys bromination Nakamura, Eiichi; Aoki, Satoshi; Sekiya, Kouichi; Oshino, Hiroji; Kuwajima, Isao; Journal of the American Chemical Society; vol. 109; nb. 26; (1987); p. 8056 - 8066 View in Reaxys

12 % Chromat.

With bromine, Time= 6h, T= 25 °C , UV-irradiation, Product distribution, Further Variations: Temperatures Vasilyev, Alexandr V.; Lindeman, Sergey V.; Kochi, Jay K.; New Journal of Chemistry; vol. 26; nb. 5; (2002); p. 582 - 592 View in Reaxys

1.5 % Chromat.

With bromine, Time= 6h, T= -20 °C , Product distribution, Further Variations: Temperatures, reaction times Vasilyev, Alexandr V.; Lindeman, Sergey V.; Kochi, Jay K.; New Journal of Chemistry; vol. 26; nb. 5; (2002); p. 582 - 592 View in Reaxys

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91 % Chromat.

With zeolite NaY, bromine in dichloromethane, Time= 5h, T= 20 °C , Bromination Smith, Keith; El-Hiti, Gamal A.; Hammond, Mark E.W.; Bahzad, Dawoud; Li, Zhaoqiang; Siquet, Christophe; Journal of the Chemical Society, Perkin Transactions 1; nb. 16; (2000); p. 2745 - 2752 View in Reaxys With hydrogen peroxide, nitric acid, potassium bromide, Ca[V(HIDA)2] in acetonitrile, Time= 6h, T= 20 °C , Bromination Reis; Silva; Frausto da Silva; Pombeiro; Chemical Communications; nb. 19; (2000); p. 1845 - 1846 View in Reaxys With sulfuric acid, hydrogen peroxide, sodium bromide in water, T= 19.84 °C , Kinetics, Further Variations: Reagents, Temperatures Sadygov; Alimardanov; Chalabiev; Russian Journal of Applied Chemistry; vol. 79; nb. 6; (2006); p. 949 - 956 View in Reaxys 96 :The following compounds presented in Example 96 was prepared in accordance with Scheme 7, by a procedure analogous to that disclosed in Examples 39 and 95, using starting materials with the appropriate substitution. Patent; REDDY US THERAPEUTICS, INC.; KALLEDA, Srinivas; PADAKANTI, Srinivas; KUMAR SWAMY, Nalivela; YELESWARAPU, Koteswar, Rao; ALEXANDER, Christopher, W.; KHANNA, Ish, Kumar; IQBAL, Javed; PILLARISETTI, Sivaram; PAL, Manojit; BARANGE, Deepak; WO2006/34473; (2006); (A2) English View in Reaxys

> 99 With gold(III) chloride, N-Bromosuccinimide in dichloromethane, Time= 11h, T= 80 °C , Inert atmosphere %Chromat. Mo, Fanyang; Yan, Jerry Mingtao; Qiu, Di; Li, Fei; Zhang, Yan; Wang, Jianbo; Angewandte Chemie - International Edition; vol. 49; nb. 11; (2010); p. 2028 - 2032 View in Reaxys 100 %Spectr.

With hydrogen peroxide, acetic acid, potassium bromide in water, Time= 6h, T= 60 °C , regioselective reaction Sharma; Sharma, Chetna; Tetrahedron Letters; vol. 51; nb. 33; (2010); p. 4415 - 4418 View in Reaxys

42 %Chromat.

With gold(III) chloride, N-Bromosuccinimide in 1,2-DICHLOROETHANE, Time= 6h, T= 60 °C Qiu, Di; Mo, Fanyang; Zheng, Zhitong; Zhang, Yan; Wang, Jianbo; Organic Letters; vol. 12; nb. 23; (2010); p. 5474 - 5477 View in Reaxys (d) General experimental procedure for oxidative bromination reaction of organic substrates using H2O2 as oxidant and KBr as bromine source at room temperature. General procedure: Catalytic reaction was carried out in a 50 mL two necked round bottom flask, which charged with 0.05 g of catalyst, substrate (2 mmol) in acetic acid (5 mL) and KBr (2.2 mmol). 30percent H2O2 (2.2 mmol) was then added drop wise to the reaction mixture. The content in the flask was stirred continuously at room temperature. After specified time of the reaction, the catalyst was filtered and the solid was washed with ether. The combined filtrates were washed with saturated sodium bicarbonate solution and then shaken with ether in a separating funnel. The organic extract was dried over anhydrous sodium sulfate. The products were analysed by Varian 3400 gas chromatograph equipped with a 30 m CP-SIL8CB capillary column and a Flame Ionization Detector. Identity of the products was also confirmed by using an Agilent GC-MS. With hydrogen peroxide, acetic acid, potassium bromide in water, Time= 6h, T= 20 °C Islam; Roy, Anupam Singha; Mondal, Paramita; Tuhina, Kazi; Mobarak, Manir; Mondal, John; Tetrahedron Letters; vol. 53; nb. 2; (2012); p. 127 - 131 View in Reaxys With sulfuric acid, hydrogen peroxide, potassium bromide in water, Time= 6h, T= 20 °C Islam, Sk. Manirul; Roy, Anupam Singha; Mondal, Paramita; Salam, Noor; Journal of Molecular Catalysis A: Chemical; vol. 358; (2012); p. 38 - 48 View in Reaxys

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95 %Chromat.

With N-Bromosuccinimide, Time= 16h, T= 80 °C Zhang, Rui; Huang, Lei; Zhang, Yanfang; Chen, Xiaorong; Xing, Weihong; Huang, Jun; Catalysis Letters; vol. 142; nb. 3; (2012); p. 378 - 383 View in Reaxys With N-Bromosuccinimide, 1,1,2,2-tetrafluoro-ethanesulfonic acid, Time= 4h, T= 20 °C Prakash, G. K. Surya; Mathew, Thomas; Panja, Chiradeep; Kulkarni, Aditya; Olah, George A.; Harmer, Mark A.; Advanced Synthesis and Catalysis; vol. 354; nb. 11-12; (2012); p. 2163 - 2171 View in Reaxys

> 99 With bromine, Time= 1.5h, T= 40 °C , Darkness, Inert atmosphere, Green chemistry %Chromat. Nishina, Yuta; Takami, Keishi; Green Chemistry; vol. 14; nb. 9; (2012); p. 2380 - 2383 View in Reaxys With hydrogen peroxide in acetic acid, Time= 5h, T= 20 °C Islam, Sk. M.; Roy, Anupam Singha; Mondal, Paramita; Salam, Noor; Paul, Sumantra; Catalysis Letters; vol. 143; nb. 2; (2013); p. 225 - 233 View in Reaxys With bromine in hexane, Time= 0.0833333h, T= 25 °C , Darkness Ross, Joanne C.; Clark, James H.; Macquarrie, Duncan J.; Barlow, Simon J.; Bastock, Tony W.; Organic Process Research and Development; vol. 2; nb. 4; (1998); p. 245 - 249 View in Reaxys Reaction Steps: 2 1: hydrochlorid acid; m-chloroperbenzoic acid 2: copper(I) bromide / acetonitrile / 2 h / 80 °C With hydrochlorid acid, m-chloroperbenzoic acid, copper(I) bromide in acetonitrile Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys Reaction Steps: 2 1: tetrafluoroboric acid; m-chloroperbenzoic acid 2: copper(I) bromide / acetonitrile / 2 h / 80 °C With tetrafluoroboric acid, m-chloroperbenzoic acid, copper(I) bromide in acetonitrile Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys Reaction Steps: 2 1: hydrogen bromide; m-chloroperbenzoic acid 2: copper(I) bromide / acetonitrile / 2 h / 80 °C With hydrogen bromide, m-chloroperbenzoic acid, copper(I) bromide in acetonitrile Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys Reaction Steps: 2 1: m-chloroperbenzoic acid 2: copper(I) bromide / acetonitrile / 2 h / 80 °C With m-chloroperbenzoic acid, copper(I) bromide in acetonitrile Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys Reaction Steps: 2 1: m-chloroperbenzoic acid 2: copper(I) bromide / acetonitrile / 2 h / 80 °C With m-chloroperbenzoic acid, copper(I) bromide in acetonitrile

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Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys With bromine Parsons, Brendon A.; Smith, Olivia Lin; Chae, Myeong; Dragojlovic, Veljko; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 980 - 993 View in Reaxys With bromine in dichloromethane-d2, T= 24.84 °C , Kinetics, Concentration, Temperature Shernyukov, Andrey V.; Genaev, Alexander M.; Salnikov, George E.; Rzepa, Henry S.; Shubin, Vyacheslav G.; Journal of Computational Chemistry; vol. 37; nb. 2; (2016); p. 210 - 225 View in Reaxys 2H 2H

2H 2H

Rx-ID: 279240 View in Reaxys 2/310 Yield 82 %

Conditions & References With Sodium bromate, sulfuric acid in water, Time= 11h, T= 0 °C Kozhushkov, Sergei I.; Yufit, Dmitry S.; Ackermann, Lutz; Organic Letters; vol. 10; nb. 16; (2008); p. 3409 - 3412 View in Reaxys

82 %

With Sodium bromate, sulfuric acid in water, Time= 11h, T= 0 - 20 °C Ackermann, Lutz; Kozhushkov, Sergei I.; Yufit, Dmitry S.; Chemistry - A European Journal; vol. 18; nb. 38; (2012); p. 12068 - 12077 View in Reaxys

75 %

With bromine, Ambient temperature Courtieu, J.; Jullien, J.; Lai, Nguyen Thoi; Guillois, A.; Gonord, P.; et al.; Journal of Chemical Physics; vol. 72; nb. 2; (1980); p. 953 - 959 View in Reaxys

75 %

With Sodium bromate, sulfuric acid in water Xu, Chunfa; Shen, Qilong; Organic Letters; vol. 16; nb. 7; (2014); p. 2046 - 2049 View in Reaxys

58 %

With gold(III) chloride in dichloromethane, Time= 24h, T= 80 °C , Inert atmosphere, Schlenk technique Zhang, Guoying; Yang, Lei; Wang, Yanyu; Xie, Yinjun; Huang, Hanmin; Journal of the American Chemical Society; vol. 135; nb. 24; (2013); p. 8850 - 8853 View in Reaxys

58 %

With gold(III) chloride, N-bromosuccinmide in 1,2-dichloro-ethane, Time= 24h, T= 80 °C Zhang, Lu; Li, Lian-Hua; Wang, Yu-Qi; Yang, Yan-Fang; Liu, Xue-Yuan; Liang, Yong-Min; Organometallics; vol. 33; nb. 8; (2014); p. 1905 - 1908 View in Reaxys

50 %

With Sodium bromate, sulfuric acid in water, T= 0 °C Li, Hu; Zhu, Ru-Yi; Shi, Wen-Juan; He, Ke-Han; Shi, Zhang-Jie; Organic Letters; vol. 14; nb. 18; (2012); p. 4850 4853,4 View in Reaxys

30 %

With bromine, silver perchlorate, magnesium oxide in pyridine Sbrana, G.; Neto, N.; Muniz-Miranda, M.; Nocentini, M.; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 39; nb. 4; (1983); p. 295 - 304

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View in Reaxys With bromine, iron Erlenmeyer; Lobeck; Epprecht; Helvetica Chimica Acta; vol. 19; (1936); p. 793 View in Reaxys With water, (R)-bromo alcohol Best; Wilson; Journal of the Chemical Society; (1946); p. 239,243 View in Reaxys With bromine Kingston, Eric E.; Shannon, James S.; Diakiw, Vladimir; Lacey, Michael J.; Organic Mass Spectrometry; vol. 16; nb. 10; (1981); p. 428 - 440 View in Reaxys With bromine, iron, Bromination Noda; Sala; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 56; nb. 1; (2000); p. 145 155 View in Reaxys With bromine, iron Wang, Ping; Wang, Fei-Fei; Chen, Yi; Niu, Qiang; Lu, Lei; Wang, Hong-Ming; Gao, Xi-Cun; Wei, Bin; Wu, Hong-Wei; Cai, Xin; Zou, De-Chun; Journal of Materials Chemistry C; vol. 1; nb. 32; (2013); p. 4821 - 4825 View in Reaxys

Rx-ID: 849122 View in Reaxys 3/310 Yield 86 %

Conditions & References With Pb3O4, trifluoroacetic acid, sodium chloride, T= 20 °C , reagents ratio, Product distribution Makhon'kov, D. I.; Cheprakov, A. V.; Rodkin, M. A.; Serguchev, Yu. A.; Davydova, V. G.; Beletskaya, I. P.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 11; (1987); p. 2424 - 2426; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 11; (1987); p. 2609 - 2611 View in Reaxys

83 %

With lead(IV) acetate, C6F13COOH, lithium chloride, Time= 7h, T= 80 °C Serguchev, Yu. A.; Davydova, V. G.; Stetsyuk, G. A.; Blendonogii, D. P.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 19; nb. 4; (1983); p. 726 - 730; Zhurnal Organicheskoi Khimii; vol. 19; nb. 4; (1983); p. 820 - 824 View in Reaxys

71 %

With thallium(III) oxide, potassium chloride in trifluoroacetic acid, Time= 7h, Ambient temperature Gun'kin, I. F.; Russian Journal of General Chemistry; vol. 67; nb. 4; (1997); p. 654 - 655; Zhurnal Obshchei Khimii; vol. 67; nb. 4; (1997); p. 699 - 700 View in Reaxys

68 %

With NaBiO3, zinc(II) chloride in acetic acid, Time= 5h, T= 20 °C Muathen, Hussni A.; Helvetica Chimica Acta; vol. 86; nb. 1; (2003); p. 164 - 168 View in Reaxys

33 %

1 : Example 1; Preparation of chlorobenzene Example 1; Preparation of chlorobenzene; Benzene (1 mmol) was treated with sodium chloride (1.2 mmol) in acetonitrile: water (2:1, 6 ml). 20percent Sulfuric acid (5 ml) and sodium periodate (20 mol percent) was added to the reaction mixture. The mixture was heated at 80° C. under inert atmosphere for 6 h. The product was purified by column chromatography to give chlorobenzene (33percent).

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With sulfuric acid, sodium chloride, sodium periodate in water, acetonitrile, Time= 6h, T= 80 °C Patent; Council of Scientific and Industrial Research; US6825383; (2004); (B1) English View in Reaxys 22 %

With Ca(OCl)2 in water, acetic acid, acetone, Time= 1h, Ambient temperature Nwaukwa, Stephen O.; Keehn, Philip M.; Synthetic Communications; vol. 19; nb. 5and6; (1989); p. 799 - 804 View in Reaxys

20 %

With sodium chlorite, trichloroacetic acid in dichloromethane, Time= 24h, Chlorination Muathen, Hussni A.; Monatshefte fur Chemie; vol. 130; nb. 12; (1999); p. 1493 - 1497 View in Reaxys

16 %

With BnNMe3 (1+)ICl4 (1-) in acetic acid, Time= 48h, T= 70 °C Kajigaeshi, Shoji; Ueda, Yasuhiro; Fujisaki, Shizuo; Kakinami, Takaaki; Bulletin of the Chemical Society of Japan; vol. 62; nb. 6; (1989); p. 2096 - 2098 View in Reaxys

10 %

With Ca(OCl)2, acetic acid in water, acetone, Time= 1h, T= 0 °C , different benzenoid compounds, Product distribution Nwaukwa, Stephen O.; Keehn, Philip M.; Synthetic Communications; vol. 19; nb. 5and6; (1989); p. 799 - 804 View in Reaxys With aluminium trichloride, SCl2, T= 60 °C , Zersetzen des Reaktionsproduktes mit Wasser Boeseken; Recueil des Travaux Chimiques des Pays-Bas; vol. 24; (1905); p. 217 View in Reaxys With hypochlorous acid, im Dunkeln Klingstedt; Acta Academiae Aboensis, Series B: Mathematica et Physica; vol. 4; nb. 2; p. 26; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 504 View in Reaxys With chlorine, tin(IV) chloride Patent; Monsanto Chem. Co.; US2111866; (1934) View in Reaxys With chlorine, iron Patent; Kroeber; DE558068; (1929); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 624 View in Reaxys Woroshzow; Silberman; Grigorjew; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 8; (1935); p. 872,875; Chem. Zentralbl.; vol. 107; nb. I; (1936); p. 2825 View in Reaxys Kriwonoss; Ukrainskii Khimicheskii Zhurnal (Russian Edition); vol. 10; (1935); p. 417; Chem. Zentralbl.; vol. 107; nb. I; (1936); p. 4897 View in Reaxys Fierz-David,H. E.; Blangey,L.; View in Reaxys Shukla et al.; ; vol. 18; (1946); p. 169 View in Reaxys With aluminium trichloride, chlorine, iron(III) chloride, sodium chloride, T= 230 - 360 °C Patent; Dow Chem. Co.; US2140550; (1938) View in Reaxys With chlorine, T= 400 - 600 °C Wibaut; van de Lande; Wallagh; Recueil des Travaux Chimiques des Pays-Bas; vol. 56; (1937); p. 65,67, 68 View in Reaxys

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Mason et al.; Journal of the Chemical Society; (1931); p. 3150,3152, 3154 View in Reaxys With hydrogenchloride, air, T= 180 - 200 °C , Leiten ueber kupferhaltige Mischkatalysatoren Patent; Raschig G.m.b.H.; DE539176; (1930); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 805,807 View in Reaxys Mathes; Angewandte Chemie; vol. 52; (1939); p. 591 View in Reaxys Patent; Raschig G.m.b.H.; US1963761; (1931) View in Reaxys With hydrogenchloride, iron oxide, 9,10-anthracenedione, Irradiation.weiteres Reagens: Sauerstoff; Sonnenlicht Patent; Kreidl, Heller and Co.; US1945067; (1930) View in Reaxys Patent; Nozicka; DE526195; (1929); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 520,523 View in Reaxys Patent; Kreidl, Heller and Co.; FR702183; (1930) View in Reaxys With hydrogenchloride, iron oxide, anthraquinone-1-sulphonic acid, Irradiation.weiteres Reagens: Sauerstoff; Sonnenlicht Patent; Kreidl, Heller and Co.; US1945067; (1930) View in Reaxys Patent; Nozicka; DE526195; (1929); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 520,523 View in Reaxys Patent; Kreidl, Heller and Co.; FR702183; (1930) View in Reaxys With hydrogenchloride, Electrolysis Ghosh et al.; Current Science; vol. 16; (1947); p. 88; ; (1947); p. 4725 View in Reaxys Jeunehomme; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 199; (1934); p. 1027; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 32; (1935); p. 173,176 View in Reaxys With nitrosyl chloride, T= 425 °C Patent; Solvay Process Co.; US2152357; (1936) View in Reaxys With nitrogen, chlorine, iron, T= 30 °C Hatta; Syozi; ; vol. 19; (1955); p. 482,486; ; (1956); p. 6 View in Reaxys With chlorine, copper, T= 20 - 300 °C Tei; Komatsu; Memoirs of the College of Science, Kyoto Imperial University; vol. <A> 10; p. 327,328; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 2370 View in Reaxys With chlorine, aluminium Meunier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 1451; Bulletin de la Societe Chimique de France; vol. <4> 27; (1920); p. 696 View in Reaxys With iodine, chlorine, iron, T= 20 - 70 °C Gindraux; Helvetica Chimica Acta; vol. 12; (1929); p. 932 View in Reaxys With hydrogenchloride, T= 45 °C , Electrolysis

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Croco; Lowy; ; vol. 50; p. 318; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 421 View in Reaxys With hydrogenchloride, methanol, Electrolysis Jayles; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 189; (1929); p. 686 View in Reaxys durch Chlorieren Fierz-David,H. E.; Blangey,L.; View in Reaxys With iodine, chlorine Jungfleisch; Annales de Chimie (Cachan, France); vol. <4> 15; (1868); p. 231,244; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1868); p. 345 View in Reaxys With chlorine, iodine cloride Jungfleisch; Annales de Chimie (Cachan, France); vol. <4> 15; (1868); p. 231,244; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1868); p. 345 View in Reaxys With aluminium trichloride, chlorine Mouneyrat; Pouret; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 127; (1898); p. 1026 View in Reaxys With pyridine, chlorine Cross; Cohen; ; p. 335; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 153 View in Reaxys With sulfuryl dichloride, T= 150 °C , im zugeschmolzenen Rohr Dubois; ; (1866); p. 705 View in Reaxys Toehl; Eberhard; Chemische Berichte; vol. 26; (1893); p. 2942 View in Reaxys With disulfur dichloride, T= 250 °C , im zugeschmolzenen Rohr Schmidt,E.; Chemische Berichte; vol. 11; (1878); p. 1173 View in Reaxys , T= 150 °C , im geschlossenen Rohr Seyewetz; Biot; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 135; (1902); p. 1121 View in Reaxys With iron(III) chloride Thomas; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 126; (1898); p. 1213; Bulletin de la Societe Chimique de France; vol. <3> 19; (1898); p. 461 View in Reaxys With iron(III) chloride, durch Chlorieren Ullmann; Cohn; View in Reaxys With iron, durch Chlorieren Ullmann; Cohn;

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View in Reaxys Behandeln mit Koenigswasser Datta; Fernandes; Journal of the American Chemical Society; vol. 36; (1914); p. 1009 View in Reaxys With hydrogenchloride, acetic acid, Electrolysis van Name; Maryott; Chem. Zentralbl.; vol. 84; nb. I; (1913); p. 1106 View in Reaxys Fichter; Glantzstein; Chemische Berichte; vol. 49; (1916); p. 2481 View in Reaxys With chlorine, iron(III) chloride Schwarz; ; vol. 5; (1954); p. 463 View in Reaxys Patent; Lummus Co.; US2470336; (1945) View in Reaxys I.G. Farbenindustrie, Bios; ; nb. 1869; (1947) View in Reaxys With hydrogenchloride, air, T= 200 - 300 °C , Leiten ueber Kupfer-Katalysatoren Woroshzow; Trawkin; Ioffe; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 11; (1938); p. 271,274; Chem. Zentralbl.; vol. 110; nb. II; (1939); p. 2765 View in Reaxys With sulfuryl dichloride, in Gegenwart von verschiedenen Katalysatoren Silberrad; Journal of the Chemical Society; vol. 119; (1921); p. 2031 View in Reaxys With aluminium trichloride, sulfuryl dichloride Boeeseken; Recueil des Travaux Chimiques des Pays-Bas; vol. 30; (1911); p. 385 View in Reaxys With aluminium amalgam, chlorine Cohen; Dakin; Journal of the Chemical Society; vol. 79; (1901); p. 1128; Journal of the Chemical Society; vol. 81; (1902); p. 1327,1347 View in Reaxys With chlorine, iron(III) chloride, iron Patent; Fahlberg, List and Co.; DE219242; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 9; p. 1179 View in Reaxys 25.4 % Chromat.

With triethyl amine hydrochloride in acetonitrile, Time= 1h, Ambient temperature Yoshida, Masato; Mochizuki, Hideki; Kamigata, Nobumasa; Chemistry Letters; (1988); p. 2017 - 2020 View in Reaxys

76 % Chromat.

With lead(IV) acetate, tin(IV) chloride in trifluoroacetic acid, Time= 2h Muathen, Hussni A.; Tetrahedron; vol. 52; nb. 26; (1996); p. 8863 - 8866 View in Reaxys

76 % Chromat.

With lead(IV) acetate, tin(IV) chloride in trifluoroacetic acid, Time= 2h, other aromatic compounds, var. solvents, var. time Muathen, Hussni A.; Tetrahedron; vol. 52; nb. 26; (1996); p. 8863 - 8866 View in Reaxys With oxygen, chlorine, T= 22.85 °C , Irradiation, Chlorination, Kinetics

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Sokolov; Hurley; Wellington; Kaiser; Platz; Nielsen; Berho; Rayez; Lesclaux; Journal of Physical Chemistry A; vol. 102; nb. 52; (1998); p. 10671 - 10681 View in Reaxys With chlorine, T= 19.85 °C , Kinetics Minsker; Malinskaya; Zakharov; Berlin; Russian Journal of Applied Chemistry; vol. 73; nb. 9; (2000); p. 1583 1587 View in Reaxys With hydrogenchloride, sodium peroxide, acetic acid in acetic anhydride, T= 24.85 °C , Kinetics Rudakova; Erykalov; Russian Journal of General Chemistry; vol. 75; nb. 5; (2005); p. 748 - 750 View in Reaxys With 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate), sodium chloride in acetonitrile, Time= 90h, T= 20 °C , Product distribution, Further Variations: Reagents, Reaction partners, reaction times Syvret, Robert G.; Butt, Kathleen M.; Nguyen, Tung P.; Bulleck, Victoria L.; Rieth, Ryan D.; Journal of Organic Chemistry; vol. 67; nb. 13; (2002); p. 4487 - 4493 View in Reaxys 1 With chlorine, Catalyst, Industry scale, Product distribution / selectivity Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2006/38705; (2006); (A1) Japanese View in Reaxys 20 %Chromat.

With sulfuryl dichloride, Time= 1.5h, T= 200 °C , Inert atmosphere Cheung, Chi Wai; Chan, Kin Shing; Organometallics; vol. 30; nb. 18; (2011); p. 4999 - 5009 View in Reaxys With hypochlorous acid in benzene-d6, Photolysis Wickramasinghe, Lasantha A.; Sharp, Paul R.; Inorganic Chemistry; vol. 53; nb. 3; (2014); p. 1430 - 1442 View in Reaxys Reaction Steps: 2 1: 3-chloro-benzenecarboperoxoic acid 2: copper(l) chloride / acetonitrile / 2 h / 80 °C With 3-chloro-benzenecarboperoxoic acid, copper(l) chloride in acetonitrile Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys

2H 2H

Rx-ID: 9310472 View in Reaxys 4/310 Yield 28 %

Conditions & References Stage 1: With n-butyllithium, potassium tert-butylate in pentane, Time= 20h, T= 0 °C Stage 2: With iodine in tetrahydrofuran, pentane, T= -75 °C , Further stages. Wang, Qian; Deredas, Dariusz; Huynh, Cyril; Schlosser, Manfred; Chemistry - A European Journal; vol. 9; nb. 2; (2003); p. 570 - 574 View in Reaxys

18 %

Stage 1: With n-butyllithium, potassium tert-butylate in hexane, Time= 20h, T= -78 - 0 °C , Inert atmosphere, Schlenk technique Stage 2: With iodine in tetrahydrofuran, hexane, Time= 0.75h, T= -78 °C , Inert atmosphere, Schlenk technique

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Nappi, Manuel; Bergonzini, Giulia; Melchiorre, Paolo; Angewandte Chemie - International Edition; vol. 53; nb. 19; (2014); p. 4921 - 4925; Angew. Chem.; vol. 126; nb. 19; (2014); p. 5021 - 5025,5 View in Reaxys With iodine, silver trifluoromethanesulfonate in dichloromethane, Time= 0.25h, T= 20 °C , Darkness Ghorai, Debasish; Choudhury, Joyanta; Chemical Communications; vol. 50; nb. 96; (2014); p. 15159 - 15162 View in Reaxys With iodine, silver trifluoromethanesulfonate in dichloromethane, Time= 0.25h, T= 20 °C , Darkness, Inert atmosphere, Schlenk technique Ge, Qingmei; Li, Bin; Song, Haibin; Wang, Baiquan; Organic and Biomolecular Chemistry; vol. 13; nb. 28; (2015); p. 7695 - 7710 View in Reaxys With iodine, silver trifluoromethanesulfonate in dichloromethane, Time= 0.25h, T= 20 °C , Inert atmosphere, Schlenk technique, Darkness Li, Renhe; Hu, Yang; Liu, Ran; Hu, Ruofang; Li, Bin; Wang, Baiquan; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3885 - 3892 View in Reaxys With iodine, silver trifluoromethanesulfonate in dichloromethane, Time= 0.25h, T= 20 °C , Darkness, Inert atmosphere Ge, Qingmei; Li, Bin; Wang, Baiquan; Organic and Biomolecular Chemistry; vol. 14; nb. 5; (2016); p. 1814 - 1821 View in Reaxys

Rx-ID: 3918646 View in Reaxys 5/310 Yield 83 %

Conditions & References With triflic acid, 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) in dichloromethane, Time= 20h, T= 40 °C , Fluorination Shamma, Tatyana; Buchholz, Herwig; Prakash, G. K. Surya; Olah, George A.; Israel Journal of Chemistry; vol. 39; nb. 2; (1999); p. 207 - 210 View in Reaxys

47 %

With Al2CuF8, T= 500 °C , Inert atmosphere, Reagent/catalyst Janmanchi, Krishna Murthy; Dolbier Jr., William R.; Organic Process Research and Development; vol. 12; nb. 2; (2008); p. 349 - 354 View in Reaxys

35 %

With CsSO4F, boron trifluoride in acetonitrile, Time= 5.5h, Ambient temperature Stavber, Stojan; Zupan, Marko; Journal of Fluorine Chemistry; vol. 17; (1981); p. 597 - 600 View in Reaxys

23.8 %

1 :Anhydrous AlF3 (ALFAAESAR, 99.5percent) and anhydrous CuF2 (ALFAAESAR, 99.5percent) were used. To a weighed amount of CuF2, AlF3 (35 mesh size) was mixed in different ratios (1:1, 1:1.5, 1:2, 1:2.5, 1:3). In a typical fluorination experiment, the metal fluoride mixture was loaded into a hastelloy reactor tube in a dry box. The reactor tube was heated to 500° C. under a flow of Ar gas. The flow rate of the carrier gas was adjusted to 25 mL/min. Vaporized benzene was passed over the heated fluoride mixture. The duration of the reaction was about 11/2 to 21/2 hrs. At the end of the reaction, the reactor tube was swept out with the carrier gas. The organic product was analyzed using HP 6890 GC/5973 Mass Spectrometer. The inorganic residue was analyzed by powder X-ray diffractometer (XRD PHILIPS APD 3720). Percentage conversions of benzene to the fluorinated products, m-fluorobenzene, flurobenzene, and o-fluorobenzene, where the amount of AlF3 increases and CuF2 remains constant are given in Table 1.; On the basis of the above results, the ratio of CuF2 to AlF3 was fixed as 1:2, and additional experiments were

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carried out at 450° C. and 425° C. The results are given in Table 2.; Introducing the benzene in fractions tested the consistency of reactivity of the fluoride bed. The results are given in Table 3. With aluminium trifluoride, CuF2, T= 425 °C , Gas phase, Product distribution / selectivity Patent; University of Florida; US2005/96489; (2005); (A1) English View in Reaxys 18 %

With AcOF in acetic acid, Time= 0.0833333h, Ambient temperature Visser, Gerard W. M.; Halteren, Bert W. v.; Herscheid, Jacobus D. M.; Brinkman, Gerard A.; Hoekstra, Arend; Journal of the Chemical Society, Chemical Communications; nb. 10; (1984); p. 655 - 656 View in Reaxys

18 %

General procedure for fluorination. General procedure: A three-necked flask equipped with an argon inlet and thermometer was loaded with arene 1 or 3—8 (10 mmol) in dry MeCN (15 mL). Then, BTFE (2.0 g, 14 mmol) was added. The mixture was cooled in the argon stream down to –35 °C and XeF2 (2.05 g, 12.5 mmol) was added in small portions. The mixture was warmed to –25 °C, stirred for 30 min at this temperature, then heated to 20 °C for 1 h, and stirred for additional 1 h (GLC control). A saturated solution of sodium bicarbonate was added to the reaction mass until termination of gas evolution. The resulted mixture was extracted with diethyl ether (3×20 mL). The extract was washed with water and dried with sodium sulfate. In the case of benzene (1), toluene (3), and chlorobenzene (4), the diethyl ether extracts were subjected to molecular distillation and fractionated, each fraction was analyzed by GLC and NMR spectroscopy. In the case of bromobenzene (5), nitrobenzene (6), p-nitrotoluene (7), and p-nitroanisole (8), the ethereal extracts were evaporated in vacuo at the temperature below 25 °C, the residue was dissolved in chloroform and subjected to flash chromatography (the eluent was hexane—chloroform, 3 : 1). The eluent was concentrated under normal pressure and the residue was analyzed by NMR spectroscopy. In the case of iodobenzene (15), a precipitate formed upon neutralization with a solution of sodium bicarbonate was filtered, washed with water, sequentially with MeCN (5 mL) and Et2O (5 mL) preserving the filtrate, and dried in air to yield a solid residue (1.1 g), which according to the NMR spectral data was a mixture consisting of (based on the weight percentages) 76percent of iodosobenzene (16) and 24percent of (4-iodophenyl)phenyliodonium tetrafluoroborate (17). Evaporation of the organic filtrate followed by the treatment of the residue with CHCl3 affords 100 mg of compound 18 with m.p. 149 °C (cf. Ref. 17: 147—149 °C). With xenon difluoride, boron trifluoride diethyl etherate in acetonitrile, Time= 2.5h, T= -35 - 20 °C , Inert atmosphere Fedorov; Zubarev; Mortikov, V. Yu.; Rodinovskaya; Shestopalov; Russian Chemical Bulletin; vol. 64; nb. 5; (2015); p. 1049 - 1052; Izv. Akad. Nauk, Ser. Khim.; nb. 5; (2015); p. 1049 - 1052,4 View in Reaxys

12 % Chromat.

With CsSO4F in acetonitrile, T= 25 °C , other solvents, reagents, reagents ratio, Product distribution, Rate constant Ip, Dominic P.; Arthur, Carol D.; Winans, Randall E.; Appelman, Evan H.; Journal of the American Chemical Society; vol. 103; nb. 8; (1981); p. 1964 - 1968 View in Reaxys With fluorine in methanol, water, other solvent (CHCl3, CCl3F, CF2COOH, CF3CH2OH); direct liquid-phase fluorination of other aromatic compounds Gambaretto, G. P.; Conte, L.; Fraccaro, C.; Napoli, M.; Journal of Fluorine Chemistry; vol. 54; nb. 1-3; (1991); p. 241 View in Reaxys

39 % Chromat.

With lead(IV) acetate, boron trifluoride diethyl etherate, mercury(II) diacetate, Ambient temperature Meio, Giuseppe V. De; Pinhey, John T.; Journal of the Chemical Society, Chemical Communications; nb. 15; (1990); p. 1065 - 1066 View in Reaxys

56 % Spectr.

With N-fluoropyridinium trifluoromethanesulfonate, Time= 24h, Heating Umemoto, Teruo; Kawada, Kosuke; Tomita, Kyoichi; Tetrahedron Letters; vol. 27; nb. 37; (1986); p. 4465 - 4468 View in Reaxys

50 % Spectr.

With N-fluorobislt;(trifluoromethyl)sulfonylgt;imide, Time= 18h, T= 22 °C

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Singh, Sukhjinder; DesMarteau, Darryl D.; Zuberi, Sharique S.; Witz, Michael; Huang, Hsu-Nan; Journal of the American Chemical Society; vol. 109; nb. 23; (1987); p. 7194 - 7196 View in Reaxys 39 % Chromat.

With lead(IV) acetate, boron trifluoride diethyl etherate, mercury(II) diacetate, Ambient temperature De Meio; Morgan; Pinhey; Tetrahedron; vol. 49; nb. 36; (1993); p. 8129 - 8138 View in Reaxys With 1-fluoro-2,4,6-trichloro-1,3,5-triazinium tetrafluoroborate in nitromethane, Time= 6h Banks, R. Eric; Besheesh, Mohamed K.; Fraenk, Wolfgang; Klapoetke, Thomas M.; Journal of Fluorine Chemistry; vol. 124; nb. 2; (2003); p. 229 - 232 View in Reaxys 2.2 With 1-fluoro-2,4,6-trichloro-1,3,5-triazinium tetrafluoroborate in [D3]acetonitrile, Time= 8h, T= 0 - 20 °C , Product distribution / selectivity Patent; AIR PRODUCTS AND CHEMICALS, INC.; EP1201627; (2002); (A1) English View in Reaxys Patent; AIR PRODUCTS AND CHEMICALS, INC.; EP1201628; (2002); (A1) English View in Reaxys With 1-fluoro-2,4,6-tris(trifluoromethyl)-1,3,5-triazinium triflate, T= -5 - 20 °C Patent; AIR PRODUCTS AND CHEMICALS, INC.; EP1201658; (2002); (A1) English View in Reaxys 4.ii With 1-fluoro-2,4,6-tris(trifluoromethyl)-1,3,5-triazinium triflate in 1,1,1,3',3',3'-hexafluoro-propanol, T= -5 - 20 °C , Product distribution / selectivity Patent; AIR PRODUCTS AND CHEMICALS, INC.; EP1201627; (2002); (A1) English View in Reaxys Patent; AIR PRODUCTS AND CHEMICALS, INC.; EP1201628; (2002); (A1) English View in Reaxys

20 %Spectr.

With tetraethylammonium fluoride tetrahydrogen fluoride, oxygen, 3-cyano-1-methylquinolinium perchlorate in [D3]acetonitrile, Time= 0.833333h, T= 20 °C , Irradiation, Sealed tube, Quantum yield, Mechanism, Kinetics Ohkubo, Kei; Fujimoto, Atsushi; Fukuzumi, Shunichi; Journal of Physical Chemistry A; vol. 117; nb. 41; (2013); p. 10719 - 10725 View in Reaxys

Rx-ID: 848952 View in Reaxys 6/310 Yield 100 %

Conditions & References With cobalt acetate tetrahydrate, trifluoroacetic acid, potassium iodide in water, Time= 0.00333333h, T= 25 °C , Mn(OAc)3 or (NH4)2Ce(SO4)3 instead Co(OAc)3; object of study: oxidative iodination promoted by Co(III), Ni(III) or Ce(IV) Makhon'kov, D. I.; Cheprakov, A. V.; Rodkin, M. A.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 1003 - 1006; Zhurnal Organicheskoi Khimii; vol. 22; nb. 6; (1986); p. 1117 - 1120 View in Reaxys

100 %

With cobalt acetate tetrahydrate, trifluoroacetic acid in water, Time= 0.00333333h, T= 25 °C Makhon'kov, D. I.; Cheprakov, A. V.; Rodkin, M. A.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 1003 - 1006; Zhurnal Organicheskoi Khimii; vol. 22; nb. 6; (1986); p. 1117 - 1120

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View in Reaxys 100 %

With iodine, silver trifluoromethanesulfonate in dichloromethane, T= 20 °C Mulholland; Zheng; Synthetic Communications; vol. 31; nb. 20; (2001); p. 3059 - 3068 View in Reaxys

98 %

With potassium permanganate, sulfuric acid, iodine in acetic acid, Time= 2.5h, T= 100 °C Chaikovskii; Novikov; Journal of applied chemistry of the USSR; vol. 57; nb. 1 pt 2; (1984); p. 121 - 123 View in Reaxys

94 %

With Pb3O4, trifluoroacetic acid, potassium iodide, T= 20 °C , reagents ratio, Product distribution Makhon'kov, D. I.; Cheprakov, A. V.; Rodkin, M. A.; Serguchev, Yu. A.; Davydova, V. G.; Beletskaya, I. P.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 11; (1987); p. 2424 - 2426; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 11; (1987); p. 2609 - 2611 View in Reaxys

91 %

With KBrO3, hydrogenchloride, potassium iodide in water, acetic acid, Time= 3h, T= 80 °C Sathiyapriya; Karunakaran, R. Joel; Journal of Chemical Research; nb. 9; (2006); p. 575 - 576 View in Reaxys

89 %

With N-iodo-succinimide, iron(III) chloride in acetonitrile, Time= 5h, T= 100 °C Tanemura, Kiyoshi; Suzuki, Tsuneo; Nishida, Yoko; Satsumabayashi, Koko; Horaguchi, Takaaki; Chemistry Letters; vol. 32; nb. 10; (2003); p. 932 - 933 View in Reaxys

88 %

With Oxonereg;, sodium iodide in water, Time= 6h, Reflux Firouzabadi; Iranpoor; Kazemi; Canadian Journal of Chemistry; vol. 87; nb. 12; (2009); p. 1675 - 1681 View in Reaxys

87 %

With trifluorormethanesulfonic acid, IPy2BF4 in dichloromethane, Time= 1h, Ambient temperature Barluenga; Gonzalez; Garcia-Martin; Campos; Tetrahedron Letters; vol. 34; nb. 24; (1993); p. 3893 - 3896 View in Reaxys

85 %

With trifluorormethanesulfonic acid, IPy2BF4 in dichloromethane, Time= 2h, Ambient temperature Barluenga, Jose; Gonzalez, Jose M.; Garcia-Martin, Miguel A.; Campos, Pedro J.; Asensio, Gregorio; Journal of Organic Chemistry; vol. 58; nb. 8; (1993); p. 2058 - 2060 View in Reaxys

83 %

With cerium(III) chloride heptahydrate, dihydrogen peroxide, sodium iodide in water, Time= 6h, Reflux, regioselective reaction Firouzabadi, Habib; Iranpoor, Nasser; Kazemi, Somayeh; Ghaderi, Arash; Garzan, Atefeh; Advanced Synthesis and Catalysis; vol. 351; nb. 11-12; (2009); p. 1925 - 1932 View in Reaxys

81 %

With sodium peroxide, hydrogen iodide in acetic acid, Time= 2h, T= 78 - 80 °C Rudakova, N. I.; Erykalov, Yu. G.; Zharikova, S. M.; Dmitrieva, E. V.; Mataradze, M. S.; Russian Journal of General Chemistry; vol. 65; nb. 2.2; (1995); p. 271 - 272; Zhurnal Obshchei Khimii; vol. 65; nb. 2; (1995); p. 315 - 317 View in Reaxys

80 %

With sulfuric acid, iodine, oxygen, nitric acid in water, Time= 6h, T= 29.9 - 49.9 °C , p= 750.06Torr , Rate constant Dorfman; Aleshkova; Russian Journal of Organic Chemistry; vol. 33; nb. 11; (1997); p. 1585 - 1597 View in Reaxys

80 %

With Ag2SO4, iodine, silver trifluoromethanesulfonate in dichloromethane, Time= 1h, Ambient temperature Sekher, Padmanabhan; Gano, James E.; Luzik Jr., Eddie D.; Synthetic Communications; vol. 27; nb. 20; (1997); p. 3631 - 3636

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View in Reaxys 80 %

With sodium lauryl sulfate, sodium iodide, Ce(OH)3OOH, Time= 3h, T= 20 °C Firouzabadi, Habib; Iranpoor, Nasser; Garzan, Atefeh; Advanced Synthesis and Catalysis; vol. 347; nb. 15; (2005); p. 1925 - 1928 View in Reaxys

79 %

With iodine, copper dichloride, aluminium trichloride, Time= 2h, T= 40 °C Sugita, Toshio; Idei, Mitsushige; Ishibashi, Yoshiyuki; Takegami, Yoshinobu; Chemistry Letters; (1982); p. 1481 - 1484 View in Reaxys

78 %

With NH4I, oxygen, NOBF4, trifluoroacetic anhydride in trifluoroacetic acid, Time= 50h, T= 25 °C Radner, Finn; Journal of Organic Chemistry; vol. 53; nb. 15; (1988); p. 3548 - 3553 View in Reaxys

77 %

With chromium(VI) oxide, sulfuric acid, iodine in acetic anhydride, acetic acid, Time= 1h, T= 55 - 65 °C , Iodination Lulinski, Piotr; Skulski, Lech; Bulletin of the Chemical Society of Japan; vol. 70; nb. 7; (1997); p. 1665 - 1669 View in Reaxys

76 %

With thallium(III) oxide, potassium iodide in trifluoroacetic acid, Ambient temperature Gun'kin, I. F.; Russian Journal of General Chemistry; vol. 67; nb. 4; (1997); p. 654 - 655; Zhurnal Obshchei Khimii; vol. 67; nb. 4; (1997); p. 699 - 700 View in Reaxys

74 %

With iodine, dinitrogen tetraoxide, carbon, iron nitrate (III), Time= 24h, T= 20 °C Firouzabadi; Iranpoor; Shiri; Tetrahedron Letters; vol. 44; nb. 49; (2003); p. 8781 - 8785 View in Reaxys

72 %

With iodine, bis-[(trifluoroacetoxy)iodo]benzene in tetrachloromethane, Time= 0.3h, Ambient temperature Merkushev, E. B.; Yudina, N. D.; Journal of Organic Chemistry USSR (English Translation); vol. 17; (1981); p. 2320 - 2322; Zhurnal Organicheskoi Khimii; vol. 17; nb. 12; (1981); p. 2598 - 2601 View in Reaxys

67 %

With dioxochloro(trimethylsiloxy)chromate(VI), iodine in dichloromethane, Time= 5h, Ambient temperature Aizpurua, J. M.; Juaristi, M.; Lecea, B.; Palomo, C.; Tetrahedron; vol. 41; nb. 14; (1985); p. 2903 - 2912 View in Reaxys

65 %

With sodium periodate, sulfuric acid, iodine in acetic anhydride, acetic acid, Time= 4h, T= 20 °C , Iodination Lulinski, Piotr; Skulski, Lech; Bulletin of the Chemical Society of Japan; vol. 73; nb. 4; (2000); p. 951 - 956 View in Reaxys

63 %

With manganese(IV) oxide, sulfuric acid, iodine, acetic anhydride in acetic acid, 1.) room temperature, 2 h, 2.) 45-55 deg C, 2 h, 3.) room temperature, overnight Lulinski, Piotr; Skulski, Lech; Bulletin of the Chemical Society of Japan; vol. 72; nb. 1; (1999); p. 115 - 120 View in Reaxys

60 %

With iodine, lithium perchlorate in various solvent(s), Ambient temperature, anodic oxidation Shono, Tatsuya; Matsumura, Yoshihiro; Katoh, Susumu; Ikeda, Kaoru; Kamada, Tohru; Tetrahedron Letters; vol. 30; nb. 13; (1989); p. 1649 - 1650 View in Reaxys

56 %

With tetraiodoglycoluril, sulfuric acid in 1,4-dioxane, Time= 0.333333h, T= 20 °C Chaikovski; Filimonov; Yagovkin; Ogorodnikov; Russian Chemical Bulletin; vol. 50; nb. 12; (2001); p. 2411 2415 View in Reaxys

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56 %

With manganese(IV) oxide, sulfuric acid, iodine in acetic anhydride, acetic acid, Time= 2h, T= 70 °C Lulinski, Piotr; Krassowska-Swiebocka, Barbara; Skulski, Lech; Molecules; vol. 9; nb. 7; (2004); p. 595 - 601 View in Reaxys

54 %

With tetrafluoroboric acid, iodine, mercury(II) oxide in dichloromethane, Time= 4h, Ambient temperature Barluenga, Jose; Campos, Pedro J.; Gonzalez, Jose M.; Asensio, Gregorio; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 11; (1984); p. 2623 - 2624 View in Reaxys

52 %

With iodine, Hg(NO3)2 in dichloromethane, Time= 14h, T= 20 °C , reactions of derivatives with var. mercury(II)-salts, Product distribution Bachki, Abderrazak; Foubelo, Francisco; Yus, Miguel; Tetrahedron; vol. 50; nb. 17; (1994); p. 5139 - 5146 View in Reaxys

52 %

With iodine, Hg(NO3)2 in dichloromethane, Time= 14h, T= 20 °C Bachki, Abderrazak; Foubelo, Francisco; Yus, Miguel; Tetrahedron; vol. 50; nb. 17; (1994); p. 5139 - 5146 View in Reaxys

52 %

With sulfuric acid, iodine, acetic anhydride in acetic acid, Time= 0.25h, T= 20 °C , oxidative iodination Kryska, Anna; Skulski, Lech; Journal of Chemical Research, Miniprint; nb. 10; (1999); p. 2501 - 2517 View in Reaxys

48 %

With IPy2BF4*2HBF4 in dichloromethane, Ambient temperature Barluenga, Jose; Gonzalez, Jose M.; Garcia-Martin, Miguel A.; Campos, Pedro J.; Asensio, Gregorio; Journal of the Chemical Society, Chemical Communications; nb. 14; (1992); p. 1016 - 1017 View in Reaxys

45 %

With dihydrogen peroxide, iodine, acetic anhydride, urea, sulfuric acid in acetic acid, T= 10 - 15 °C Lulinski, Piotr; Kryska, Anna; Sosnowski, Maciej; Skulski, Lech; Synthesis; nb. 3; (2004); p. 441 - 445 View in Reaxys

40 %

With Na2CO3*1.5H2O2, sulfuric acid, iodine, acetic anhydride, acetic acid, Time= 2h, T= 45 - 50 °C Zielinska, Agnieszka; Skulski, Lech; Molecules; vol. 10; nb. 10; (2005); p. 1307 - 1317 View in Reaxys

37 %

With Bi(NO3)3, iodine, silica gel, Time= 72h, T= 20 °C Alexander, Varughese M.; Khandekar, Amit C.; Samant, Shriniwas D.; Synlett; nb. 12; (2003); p. 1895 - 1897 View in Reaxys

31 %

With dicloroiodoisocyanuric acid in acetonitrile, Time= 1608h, T= 20 °C , Darkness, regioselective reaction Da Silva Ribeiro, Rodrigo; Esteves, Pierre M.; De Mattos, Marcio C.S.; Journal of the Brazilian Chemical Society; vol. 23; nb. 2; (2012); p. 228 - 235 View in Reaxys

26 %

With aluminum oxide, iodine in solid, Time= 20h, Ambient temperature Boothe, Richard; Dial, Christopher; Conaway, Richard; Pagni, Richard M.; Kabalka, George W.; Tetrahedron Letters; vol. 27; nb. 20; (1986); p. 2207 - 2210 View in Reaxys

13 %

With AgNO2, iodine in dichloromethane, Time= 72h, Ambient temperature, investigation of iodination of var. alkylbenzenes, Product distribution Sy, Wing-Wah; Lodge, Bruce A.; Tetrahedron Letters; vol. 30; nb. 29; (1989); p. 3769 - 3772 View in Reaxys

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4.7 %

With iodine, Time= 20h, T= 22 °C , other aromatic hydrocarbons, alkenes, alkynes; var. temperatur, time, reagents, Product distribution, Mechanism Pagni, Richard M.; Kabalka, George W.; Boothe, Richard; Gaetano, Kevan; Stewart, Lyman J.; et al.; Journal of Organic Chemistry; vol. 53; nb. 19; (1988); p. 4477 - 4482 View in Reaxys With iodine, fluorine in chloroform, monofluoro-trichloromethane, Time= 24h, T= -78 °C , other aromatic compounds Rozen, Shlomo; Zamir, Dov; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3552 - 3555 View in Reaxys With aluminum oxide, iodine, Time= 20h, investigations of the influence of the factors (reaction time, reaction temperature and the extent of dehydration of the alumina) to the product yields, Product distribution Boothe, Richard; Dial, Christopher; Conaway, Richard; Pagni, Richard M.; Kabalka, George W.; Tetrahedron Letters; vol. 27; nb. 20; (1986); p. 2207 - 2210 View in Reaxys

99 % Chromat.

With Pb4(OAc)4, iodine, trifluoroacetic acid, prototype reaction, oth. benzene derivatives, oth. reagent (alkali-metal iodide), intermediate, Rate constant Serguchev, Yu. A.; Davydova, V. G.; Makhon'kov, D. I.; Cheprakov, A. V.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 9; (1985); p. 1841; Zhurnal Organicheskoi Khimii; vol. 21; nb. 9; (1985); p. 2010 - 2011 View in Reaxys With silver salt, iodine Birckenbach; Goubeau; Berninger; Chemische Berichte; vol. 65; (1932); p. 1339,1343 View in Reaxys Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys With iodine, nitric acid Roedig; ; vol. 5/4; (1960); p. 573 View in Reaxys Dains; Brewster; ; Vol. I <2. Ausg. 1941> 323 View in Reaxys With sulfuric acid, iodine, nitric acid, acetic acid Varma; Sreenivasmurthyachar; Journal of the Indian Chemical Society; vol. 13; (1936); p. 187 View in Reaxys With (NH4)2S2O8, iodine, sodium acetate Marko; Beljajew; ; vol. 3; nb. 4; (1939); p. 3; ; (1943); p. 6250 View in Reaxys With iodine, copper dichloride Marko; Beljajew; ; vol. 3; nb. 4; (1939); p. 3; ; (1943); p. 6250 View in Reaxys With iodine, silver sulphate Marko; Beljajew; ; vol. 3; nb. 4; (1939); p. 3; ; (1943); p. 6250 View in Reaxys With sulfuric acid, iodine, nitric acid, acetic acid Nowikow; Zhurnal Obshchei Khimii; vol. 24; (1954); p. 655; engl. Ausg. S. 665

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View in Reaxys With iodine, silver trifluoroacetate Haszeldine; Sharpe; Journal of the Chemical Society; (1952); p. 993,1000 View in Reaxys With nitrosulfuric acid, acetic acid, durch Jodierung Varma; Kulkarni; ; vol. 3; p. 294; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 1432 View in Reaxys With sulfuric acid, acetic acid, sodium nitrite, durch Jodierung Varma; Panikar; ; vol. 3; p. 343; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 1432 View in Reaxys With KIO3, sulfuric acid Peltzer; Justus Liebigs Annalen der Chemie; vol. 136; (1865); p. 201 View in Reaxys With sulfuric acid, iodine Istrati; Georgescu; Chemiker-Zeitung, Chemische Apparatur; vol. 1; p. 56; 16 Repert. <1892>, 102 View in Reaxys Istrati; Bulletin de la Societe Chimique de France; vol. <3> 5; (1891); p. 159; ; vol. 1; p. 17 View in Reaxys Neumann; Justus Liebigs Annalen der Chemie; vol. 241; (1887); p. 84 View in Reaxys With iodine, iron(III) chloride, T= 100 °C Meyer,L.; Justus Liebigs Annalen der Chemie; vol. 231; (1885); p. 195; Journal fuer Praktische Chemie (Leipzig); vol. <2> 34; (1886); p. 504 View in Reaxys With aluminium trichloride, iodine cloride Greene; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 90; (1880); p. 41 View in Reaxys With sodium peroxodisulphate, iodine, acetic acid Elbs; Jaroslawzew; Journal fuer Praktische Chemie (Leipzig); vol. <2> 88; (1913); p. 92 View in Reaxys With iodine, nitric acid, T= 50 °C Datta; Chatterjee; Journal of the American Chemical Society; vol. 39; (1917); p. 437 View in Reaxys Organic Synthesees; View in Reaxys With iodic acid Peltzer; Justus Liebigs Annalen der Chemie; vol. 136; (1865); p. 201 View in Reaxys With iodosulfur, nitric acid Edinger; Goldberg; Chemische Berichte; vol. 33; (1900); p. 2884 View in Reaxys Patent; Kalle and Co.; DE123746 View in Reaxys With iodine, fluorine in chloroform, monofluoro-trichloromethane, Time= 24h, T= -78 °C , Yield given

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Rozen, Shlomo; Zamir, Dov; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3552 - 3555 View in Reaxys 79 % Chromat.

With tetrabutyl ammonium fluoride, iodine, trifluoroacetic acid in 1,2-dichloro-ethane, electrolysis Lines, Robert; Parker, Vernon D.; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 34; nb. 1; (1980); p. 47 - 52 View in Reaxys

90 % Chromat.

With XeF2, iodine in dichloromethane, Time= 1.5h, Ambient temperature Shellhamer, Dale F.; Jones, Brian C.; Pettus, Benjamin J.; Pettus, Tobiah L.; Stringer, Joy Merry; Heasley, Victor L.; Journal of Fluorine Chemistry; vol. 88; nb. 1; (1998); p. 37 - 39 View in Reaxys

88 % Spectr.

With dipotassium peroxodisulfate, iodine in dichloromethane, trifluoroacetic acid, Time= 69h, T= 36 - 38 °C Hossain, Md. Delwar; Oyamada, Juzo; Kitamura, Tsugio; Synthesis; nb. 5; (2008); p. 690 - 692 View in Reaxys With iodine, mercury(II) oxide in dichloromethane Liang, Zhidan; Hou, Weizhe; Du, Yunfei; Zhang, Yongliang; Pan, Yan; Mao, Deng; Zhao, Kang; Organic Letters; vol. 11; nb. 21; (2009); p. 4978 - 4981 View in Reaxys

74 %Chromat.

With cerium (IV) oxide, dihydrogen peroxide, iodine in water, pH= 1.5, Reflux Zhang, Peng; Sun, Dongqing; Wen, Mingwei; Yang, Jingkui; Zhou, Kebin; Wang, Zhixiang; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 720 - 729 View in Reaxys

I I

Rx-ID: 29546785 View in Reaxys 7/310 Yield

Conditions & References 1 :Comparative Example 1; In the system shown in FIG. 1, benzene (26.4 g/hr) and iodine (42.9 g/hr) were fed into a reactor without adding monoiodobenzene, and were subjected to a continuous iodination process under conditions of a reaction temperature of 280° C. and atmospheric pressure. 24 hours after the reaction conditions were reached, sampling and analysis were performed. The experimental conditions and results are shown in Table 1 below. With iodine, oxygen, zeolite catalyst, Time= 24h, T= 280 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; US2010/185031; (2010); (A1) English View in Reaxys 3 :Example 3; In the equipment as shown in Fig. 2, benzene (91.3 g/hr), iodine (47.87 g/hr), and monoiodo benzene (422.7 g/hr) were introduced to perform iodination in the presence of Na-13X zeolite catalyst under the same conditions as in Comparative Example 1. In addition, diiodo benzene (162.2 g/hr) was also introduced, and the composition of diiodo benzene was 22percent (wtpercent), based on the total feed materials. At this time, the molar ratio of non-halogenated aromatic compound/iodine introduced was 1.93. Further, a temperature distribution graph according to a length of the reactor, measured at the center of the reactor in the same manner as in Comparative Example 1, is shown in Fig. 4. The reaction conditions and data of the reaction products are shown in the following Table 1. In particular, all areas of the reactor were maintained at an almost constant temperature. The temperature of the upper part of the reactor was maintained at approximately 300 °C or lower, which is close to the desired temperature. The reaction temperature was also maintained at approximately 275 °C or higher along with the flow direction of the reactant. With iodine, oxygen, Na-13X zeolite, T= 275 - 300 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK Chemicals, Co., Ltd.; EP2374778; (2011); (A2) English View in Reaxys

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I Si

Rx-ID: 3858622 View in Reaxys 8/310 Yield

Conditions & References

75 %

With iodosylbenzene, boron trifluoride diethyl etherate in dichloromethane, Time= 3h, T= 0 °C Lee, Kilsung; Kim, Dae Young; Oh, Dong Young; Tetrahedron Letters; vol. 29; nb. 6; (1988); p. 667 - 668 View in Reaxys

F F

(v2)

Rx-ID: 26403747 View in Reaxys 9/310 Yield 68 %

Conditions & References in tetrachloromethane, in presence of a trace of HF; Shaw; Hyman; Journal of the American Chemical Society; vol. 91; (1969); p. 1563 View in Reaxys anonymous; Chemical and Engineering News; vol. 47; nb. Sep. 2; (1969); p. 45 - 45 View in Reaxys vol. He: Edelgasverb.; 1.8.1.2.2, page 29 - 32 ; (from Gmelin) View in Reaxys

P 0.5

(v4) (v4)

(v4)

Pd2+ SP-4 (v4) (v4) C – (v4)C – F

(v4)

Pd2+ SP-4 C – (v4)Cl – (v1) F F

(v4)

Rx-ID: 27547098 View in Reaxys 10/310 Yield 90 %

Conditions & References in chlorobenzene, under N2 atm. mixt. Pd complex and PhCl was heated at 140°C for 2h; mixt. was layered with hexane Grushin, Vladimir V.; Marshall, William J.; Journal of the American Chemical Society; vol. 128; nb. 14; (2006); p. 4632 - 4641 ; (from Gmelin) View in Reaxys

Rx-ID: 849124 View in Reaxys 11/310 Yield 75 %, 5 %

Conditions & References With N-chloro-succinimide, iron(III) chloride in acetonitrile, Time= 2h Tanemura, Kiyoshi; Suzuki, Tsuneo; Nishida, Yoko; Satsumabayashi, Koko; Horaguchi, Takaaki; Chemistry Letters; vol. 32; nb. 10; (2003); p. 932 - 933 View in Reaxys With tetrachloromethane, ICl3 Campaigne; Thompson; Journal of the American Chemical Society; vol. 72; (1950); p. 629 View in Reaxys 1 : EXAMPLE 1 EXAMPLE 1 [0035] Engineering calculations were made to determine the yield of styrene produced from benzene by the present process. With reference to the flowsheet of FIG. 1, 100 lb. of benzene was fed to R1. Sufficient hydrogen chloride and oxygen were used to react 50percent of the benzene so that 39.8percent of the benzene feed was con-

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verted to chlorobenzene, 10.0percent was converted to dichlorobenzene and 0.2percent was lost due to combustion. (In U.S. Pat. No. 1,963,761 it was noted that "combustion of the benzene practically does not occur".) The resulting chlorinated benzenes were passed to R2 where they were pyrolyzed to give styrene, benzene and some tars. The efficiency of these reactions was assumed to be 98percent. By recycling the unreacted benzene from R1 and the benzene formed in R2, 130 lb. of styrene was produced to give an overall conversion of 97.8percent. This result compared favorable with conventional processes that are reported to achieve yields of 86 to 92percent. With hydrogenchloride, oxygen Patent; Stauffer, John E.; US2004/73067; (2004); (A1) English View in Reaxys -1 F

(v4)

B FF

N+

Rx-ID: 9819458 View in Reaxys 12/310 Yield 54 %, 26 % Chromat.

Conditions & References With xanthone powder in acetonitrile, T= 20 °C , Photolysis Milanesi, Silvia; Fagnoni, Maurizio; Albini, Angeld; Journal of Organic Chemistry; vol. 70; nb. 2; (2005); p. 603 610 View in Reaxys

I I

Rx-ID: 28519056 View in Reaxys 13/310 Yield

Conditions & References 1 :Comparative Example 1; The iodinating reactor shown in Fig. 1 was used, and without adding DIB, only the benzene (176.4g/hr), iodine (I2) (275.0g/hr), and air were reacted. The iodine (I2) and the air went through the preheater and were heated to 200°C and then supplied to the iodinating reactor (ROl). Further, benzene was also heated to 200°C and supplied in the form of a vapor, using the other feeding line. The reaction temperature of the iodinating reactor was controlled by controlling the temperature of oil supplied to the oil jacket. And the temperature of the iodinating reactor, which was measured at the inner center of the reactor, was adjusted to be constant at 280°C. Nevertheless, the reaction temperature was not maintained constantly. The temperature of the upper part of the iodinating reactor was higher <n="19"/>than preferable. And, the temperature of the iodinating reactor went down along with the flow direction of the reactant. To examine temperature profile of the iodinating reactor, a temperature measuring instrument such as a thermowell and a thermocouple was installed at the inner center of the iodinating reactor. The temperature of the upper, middle, and lower parts of the iodinating reactor was then periodically examined using the movable thermocouple, which can move upward and downward of the iodinating reactor to determine the highest temperature region. The reaction was carried out in the normal temperature for 24 hours after reaching the reaction condition. Then, sampling and analyzing were conducted after the iodination, and the reaction conditions and results are shown in the following Table 1.; Example 1; <n="20"/>The iodinating reactor shown in Fig. 2 was used, and except that the benzene (565.2g/hr), di-iodo benzene (83.4g/hr), and iodine (I2) (900.1g/hr) were supplied to the iodinating reactor (ROl), all of the reaction conditions were adjusted to be the same as in Comparative example 1. The reaction conditions and reaction results are shown in the following Table 1. The used DIB was obtained from a mother liquor of three kinds of isomers (p-, o~, and nr) , which was separated from pure crystallized solid p-DIB. With iodine, oxygen, zeolite catalyst, Time= 24h, T= 25 - 280 °C , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2009/78667; (2009); (A2) English View in Reaxys 2 :Example 2; Except that the benzene, water, and iodine (I2) were supplied at 550.0g/hr, 35g/hr, and 744.1g/hr, respectively, all of the reaction conditions were adjusted to be the same as in Comparative Example 1. The reaction conditions and the reaction results are shown in the following Table 1. With iodine, oxygen, zeolite catalyst in water, Time= 24h, T= 25 - 280 °C , Product distribution / selectivity

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Patent; SK CHEMICALS CO., LTD.; WO2009/78667; (2009); (A2) English View in Reaxys F F

Rx-ID: 34235094 View in Reaxys 14/310 Yield

Conditions & References With silver(II) fluoride in dichloromethane, Time= 72h, T= 20 °C , Inert atmosphere, Molecular sieve Durie, Alastair J.; Slawin, Alexandra M. Z.; Lebl, Tomas; O'Hagan, David; Angewandte Chemie, International Edition; vol. 51; nb. 40; (2012); p. 10086 - 10088,3; Angewandte Chemie; vol. 124; nb. 40; (2012); p. 10233 10235,3 View in Reaxys

I+

I–

Rx-ID: 5082435 View in Reaxys 15/310 Yield 44 %, 10 %

Conditions & References With chromium(VI) oxide, sulfuric acid, iodine in acetic anhydride, acetic acid, T= 20 - 45 °C , Iodination Lulinski, Piotr; Skulski, Lech; Bulletin of the Chemical Society of Japan; vol. 70; nb. 7; (1997); p. 1665 - 1669 View in Reaxys

I I

Rx-ID: 28134547 View in Reaxys 16/310 Yield

Conditions & References 1 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity. With HY(Si/Al molar ratio is 5), Time= 8h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 4 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity. With HBeta(Si/Al molar ratio is 25), Time= 8h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys

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3 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity. With HX, Time= 8h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 2; 5; 6; 7; 8 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity.; Examples 5 and 6, and Comparative Example 5To investigate the effect of transiodination temperature, these examples were evaluated substantially the same as Example 2 except that the transiodination temperatures were 1200C (Example 5), 180°C (Example 6), and 100 "C (Comparative Example 5). The selectivities to MIB with the passage of reaction time were measured and are shown in Fig. 2.As shown in Fig. 2, when the reaction temperature was lower the selectivity to MIB was higher, but the catalyst activity decreased rapidly due to coke deposited in the catalyst. That is, when the temperature was lower than 120 "C (Comparative Example 5), the catalyst activity decreased rapidly with the passage of the reaction time. On the other hand, when the temperature was at 120 0C or higher (Examples 5), the initial selectivity to MIB began to decrease slowly. When the reaction was performed for a long time at 180 0C or higher (Example 6), the catalyst activity did not decrease.; Examples 7 and 8. and Comparative Examples 6 and 7 To investigate the effect of feed composition, these examples were evaluated substantially the same as the Example 2 except that the feeds were Reactant 1 (Example 7), Reactant 2 (Example 8), Reactant 3 (Comparative Example 6), and Reactant 4 (Comparative Example 7). The selectivity to MIB with the passage of reaction time were measured and shown in Fig. 3.As seen from Fig. 3, the reactants of Examples 7 and 8 with molar ratios of benzene/Feed of 2:1 or higher showed superior selectivity to MIB with no catalyst inactivation. However, the reactants of Comparative Examples 6 and 7 with molar ratios of benzene/ Feed of lower than 2:1 showed low selectivity toMIB and a decrease of catalyst activity with the passage of reaction time. With HY(Si/Al molar ratio is 12), Time= 8 - 200h, T= 100 - 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 3 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity. With HY(Si/Al molar ratio is 80), Time= 8h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 1 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of

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HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity. With HZCM-5 (Si/Al molar ratio is 25), Time= 8h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 2 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity. With Na-ZCM-5 (Si/Al molar ratio is 25), Time= 8h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 9 :Example 9The transiodination in Example 7 was performed until the catalyst was inactivated. Then, the inactivated catalyst was recycled by calcining at 4850C for 12 hours in an air atmosphere. The transiodination was carried out with recycled catalyst under the same conditions as of Example 7.The selectivities to MIB in Example 7 using a fresh catalyst and Example 9 using the recycled catalyst are shown in Fig. 4. As shown in Fig. 4, the selectivity to MIB in Example 7 was maintained consistently at 90percent or more for up to 80 hours of reaction time, but decreased slowly after 80 hours, which was similar to the selectivity of Example 9 using the recycled catalyst.These examples confirmed that the recycling of the catalyst caused the catalyst activity to be recovered. The recovery efficiency of the catalyst was very high, and thus the catalyst can be reused several times without detrimental <n="15"/ >effects.The preparation method of the present invention is advantageous in recovering iodine from m-di-iodo benzene, o-di-iodo benzene, and tri-iodo benzene, which are obtained in general production of p-di-iodo benzene as byproducts, while minimizing the loss of iodine. With inactivated HY(Si/Al molar ratio is 12); calcined at 485 C for 12h, Time= 200h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 2 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity. With aluminum oxide, Time= 8h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys

I I

Rx-ID: 3918655 View in Reaxys 17/310 Yield 8.7 %, 1.5 %, 56 %

Conditions & References With diiodine pentaoxide, sulfuric acid, iodine in acetic acid, Time= 40h, T= 60 °C Brazdil, Linda C.; Cutler, Carlo J.; Journal of Organic Chemistry; vol. 61; nb. 26; (1996); p. 9621 - 9622

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View in Reaxys 46 %, 8.6 %, 45 %

With diiodine pentaoxide, sulfuric acid, iodine in acetic acid, Time= 24h Brazdil, Linda C.; Fitch, Jill L.; Cutler, Carlo J.; Haynik, Denise M.; Ace, Eryn R.; Journal of the Chemical Society. Perkin Transactions 2; nb. 4; (1998); p. 933 - 936 View in Reaxys

45 %, 46 %, 8 %

With diiodine pentaoxide, sulfuric acid, iodine in acetic acid, Time= 40h, T= 60 °C Brazdil, Linda C.; Cutler, Carlo J.; Journal of Organic Chemistry; vol. 61; nb. 26; (1996); p. 9621 - 9622 View in Reaxys

45 %, 46 %, 8.6 %

45 %, 8.0 %, 46 %

45 %, 8.6 %, 46 %

30 %, 40 %, 30 %

With iodine, fluorine in chloroform, monofluoro-trichloromethane, Time= 5h, T= 25 °C Rozen, Shlomo; Zamir, Dov; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3552 - 3555 View in Reaxys

30 %, 30 %, 40 %

With iodine, fluorine in chloroform, monofluoro-trichloromethane, Time= 5h, T= 25 °C Rozen, Shlomo; Zamir, Dov; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3552 - 3555 View in Reaxys With iodine, fluorine in chloroform, monofluoro-trichloromethane, Time= 5h, T= 25 °C , other aromatic compounds Rozen, Shlomo; Zamir, Dov; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3552 - 3555 View in Reaxys

2.99 g, 0.13 g, 0.01 g

With sodium o-vanadate, air, trifluorormethanesulfonic acid, iodine, Time= 1.5h, T= 100 °C , p= 7355.08Torr , other metal salt and oxides as catalyst (Fe(2+), Fe(3+), Cu(2+), V(3+), V(5+), Ti(4+), Zr(4+), Ni(2+), Pd(2+), Zn(2+), Cd(2+) Ag(1+), Tl(1+), Mn(4+), Sb(3+)), pressure from 2 to 10 kg/cm2, reaction time from 1.5 to 9 h, CF3CO2H, CH3SO3H as solvents, Product distribution Shimizu, Atsushi; Yamataka, Kazunori; Isoya, Toshiro; Bulletin of the Chemical Society of Japan; vol. 58; nb. 5; (1985); p. 1611 - 1612 View in Reaxys With diiodine pentaoxide, sulfuric acid, iodine in acetic acid, T= 323 - 343 °C , influence of I2, H2SO4 conc., Kinetics Brazdil, Linda C.; Fitch, Jill L.; Cutler, Carlo J.; Haynik, Denise M.; Ace, Eryn R.; Journal of the Chemical Society. Perkin Transactions 2; nb. 4; (1998); p. 933 - 936 View in Reaxys

0.13 g, 0.01 g, 2.99 g

With sodium o-vanadate, air, trifluorormethanesulfonic acid, iodine, Time= 1.5h, T= 100 °C , p= 7355.08Torr Shimizu, Atsushi; Yamataka, Kazunori; Isoya, Toshiro; Bulletin of the Chemical Society of Japan; vol. 58; nb. 5; (1985); p. 1611 - 1612 View in Reaxys

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H 13C H 13C

13C

13CH

H 13C

13CH

H 13C

13C

13CH

Rx-ID: 8943488 View in Reaxys 18/310 Yield 70 %

Conditions & References With 1,3-dibromo-5,5-dimethyl-hydantoin, trifluorormethanesulfonic acid in dichloromethane Diel, Bruce N.; Han, Mingcheng; Kole, Panna L.; Boaz, David B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 50; nb. 5-6; (2007); p. 551 - 553 View in Reaxys With 1,3-dibromo-5,5-dimethyl-hydantoin, trifluorormethanesulfonic acid in dichloromethane, Time= 2h, Heating Zippi, Elizabeth M.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 44; nb. 11; (2001); p. 757 761 View in Reaxys

F F

F S F

O F

Rx-ID: 10779132 View in Reaxys 19/310 Yield

Conditions & References 1; 2; 3 :Example 1Preparation of C6H5OSF5 (Excess C6H6, No Solvent)Into a 50-cc stirred reactor (Parr Instrument Co.) were loaded 21.75 g (76.0 mmol) SF5OOSF5 and 11.95 g C6H6 (153 mmol). The mixture was heated to 125° C. and stirred at temperature for about 18 hours. After the specified time, the reactor and contents were cooled and vented. The reaction product was poured into a beaker containing cold 20percent aqueous KOH and the immiscible denser liquid portion (product) was separated by decantation. Analysis of the product by GC-MS revealed a product distribution (normalized) containing residual benzene (C6H6=37.5percent), fluorobenzene (C6H5F=9.2percent), oxypentafluorosulfanyl benzene (C6H5OSF5=50.1percent), oxypentafluorosulfanylfluorobenzene (C6H4FOSF5=0.9percent), bis(oxypentafluorosulfanyl)benzene (C6H4(OSF5)2=2.3percent) as well as other minor products.; Example 2Preparation of C6H5OSF5 (Near-stoichiometric C6H6, No Solvent)Into a 50-cc stirred reactor (Parr Instrument Co.) were loaded 23.02 g (80.5 mmol) SF5OOSF5 and 6.41 g C6H6 (82.1 mmol). The mixture was heated to 124° C. and stirred at temperature for about 4 hours. After the specified time, the reactor and contents were cooled and vented. The reaction product was poured into a beaker containing cold water and subsequently neutralized with aqueous bicarbonate. The product was extracted into CH2Cl2 and separated by decantation. Analysis of the product by GCMS revealed a product distribution (normalized) containing residual benzene (C6H6=29.8percent), fluorobenzene (C6H5F=6.4percent), oxypentafluorosulfanyl benzene (C6H5OSF5=57.7percent), oxypentafluorosulfanylfluorobenzene (C6H4FOSF5=3.6 percent), bis(oxypentafluorosulfanyl)benzene (C6H4(OSF5)2=2.5percent) as well as other minor products.; Example 3Preparation of C6H5OSF5 (Stoichiometric C6H6, No Solvent)The method of Example 2 was repeated, with 25.07 g (87.6 mmol) SF5OOSF5 and 6.85 g (87.7 mmol) C6H6 heated to 125° C. for 5 hours. Analysis by GC-MS after workup revealed a product distribution (normalized) containing residual benzene (C6H6=25.0percent), fluorobenzene (C6H5F=10.3percent), oxypentafluorosulfanyl benzene (C6H5OSF5=50.0percent), oxypentafluorosulfanylfluorobenzene (C6H4FOSF5=9.5percent), bis(oxypentafluorosulfanyl)benzene (C6H4(OSF5)2=5.3percent) as well as other minor products. With bis(pentafluorosulfur) peroxide, Time= 4 - 18h, T= 124 - 125 °C , Product distribution / selectivity Patent; Syvret, Robert George; Lal, Gauri Sankar; US2008/9653; (2008); (A1) English View in Reaxys 4 :Into a 50-cc stirred reactor (Parr Instrument Co.) were loaded 14.9 g (52.1 mmol) SF5OOSF5, 4.5 g C6H6 (57.6 mmol), and 20 mL Freon.(R).-113 (F-113). The was heated to 150° C. and stirred at temperature for about 15 hours. After the specified time, the reactor and contents were cooled and vented. The reaction product was poured into a beaker containing cold 20percent aqueous KOH and the immiscible denser liquid portion (product) was separated by decantation. Analysis of the product by GC-MS revealed a product distribution (normalized) containing residual benzene (C6H6=52.5percent), fluorobenzene (C6H5F=10.0percent), oxypentafluorosulfanyl benzene (C6H5OSF5=33.6percent), oxypentafluorosulfanylfluorobenzene (C6H4FOSF5=2.9percent), bis(oxypentafluorosulfanyl)benzene (C6H4(OSF5)2=1.0percent) as well as other minor products.

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With bis(pentafluorosulfur) peroxide in Freonreg;-113, Time= 15h, T= 150 °C Patent; Syvret, Robert George; Lal, Gauri Sankar; US2008/9653; (2008); (A1) English View in Reaxys

Rx-ID: 23313387 View in Reaxys 20/310 Yield 40.5 - 63.1 %, 1.4 3.4 %, 2.4 - 5.4 %

Conditions & References 1 :Anhydrous AlF3 (ALFAAESAR, 99.5percent) and anhydrous CuF2 (ALFAAESAR, 99.5percent) were used. To a weighed amount of CuF2, AlF3 (35 mesh size) was mixed in different ratios (1:1, 1:1.5, 1:2, 1:2.5, 1:3). In a typical fluorination experiment, the metal fluoride mixture was loaded into a hastelloy reactor tube in a dry box. The reactor tube was heated to 500° C. under a flow of Ar gas. The flow rate of the carrier gas was adjusted to 25 mL/min. Vaporized benzene was passed over the heated fluoride mixture. The duration of the reaction was about 11/2 to 21/2 hrs. At the end of the reaction, the reactor tube was swept out with the carrier gas. The organic product was analyzed using HP 6890 GC/5973 Mass Spectrometer. The inorganic residue was analyzed by powder X-ray diffractometer (XRD PHILIPS APD 3720). Percentage conversions of benzene to the fluorinated products, m-fluorobenzene, flurobenzene, and o-fluorobenzene, where the amount of AlF3 increases and CuF2 remains constant are given in Table 1.; On the basis of the above results, the ratio of CuF2 to AlF3 was fixed as 1:2, and additional experiments were carried out at 450° C. and 425° C. The results are given in Table 2.; Introducing the benzene in fractions tested the consistency of reactivity of the fluoride bed. The results are given in Table 3. With aluminium trifluoride, CuF2, T= 450 - 500 °C , Gas phase, Product distribution / selectivity Patent; University of Florida; US2005/96489; (2005); (A1) English View in Reaxys 2 : Fluorination of Benzene Utilizing AlF3 and MF2 (M=Ca, Zn, Mg) as the Fluorinating Agent EXAMPLE 2 Fluorination of Benzene Utilizing AlF3 and MF2 (M=Ca, Zn, Mg) as the Fluorinating Agent Additional fluorination experiments using other materials such as CaF2, ZnF2, MgF2 and activated carbon as additives were carried out. When benzene was treated with the activated carbon added copper fluoride, no fluorination was observed. The experimental conditions as mentioned in Example 1 were followed and the results are presented in Table 4. With fluorspar, T= 500 °C , Gas phase, Product distribution / selectivity Patent; University of Florida; US2005/96489; (2005); (A1) English View in Reaxys 2 :Additional fluorination experiments using other materials such as CaF2, ZnF2, MgF2 and activated carbon as additives were carried out. When benzene was treated with the activated carbon added copper fluoride, no fluorination was observed. The experimental conditions as mentioned in Example 1 were followed and the results are presented in Table 4. With MgF2, T= 500 °C , Gas phase, Product distribution / selectivity Patent; University of Florida; US2005/96489; (2005); (A1) English View in Reaxys

Rx-ID: 29102881 View in Reaxys 21/310 Yield 50 %, 5 %

Conditions & References 2 :Example 2; Fluorination of BenzeneFluorination of benzene is carried out utilizing co-precipitated copper aluminum fluoride (CuAl01), commercial CuF2 (Aldrich), AlF3 (Aldrich) and a mixture of copper fluoride aluminum fluoride. 2.5 g of metal fluoride/fluoride mixture was loaded into a haste alloy reactor tube in a dry box. The sample was pretreated under a flow of argon gas (25 ml/min) for 6 h at 450° C. 0.5 ml of benzene was introduced in to the reactor

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using a septum in each pass along with the carrier gas (argon, 40 ml/min) at 500° C. The reactor outlet was connected to a cold-trap and the product mixture was condensed for 30 min for each pass of benzene and analyzed using gas chromatography (HP6890) and F19-NMR. Percentage conversions of benzene to fluorinated products are given in Table 1. With co-precipitated copper aluminum fluoride (CuAl01), T= 500 °C , Inert atmosphere, Gas phase, Product distribution / selectivity Patent; University of Florida Research Foundation Inc.; US2010/16607; (2010); (A1) English View in Reaxys F

F F

F O S

F O

F F

Rx-ID: 3917834 View in Reaxys 22/310 Yield 88 %

Conditions & References in chloroform-d1, Time= 0.166667h, T= 60 °C , sealed in vacuo Banks, Ronald Eric; Khazaei, Ardeshir; Journal of Fluorine Chemistry; vol. 46; nb. 2; (1990); p. 297 - 305 View in Reaxys

Rx-ID: 3918726 View in Reaxys 23/310 Yield 36.5 %, 4.0 %, 2.6 %, 53.8 %

Conditions & References With chlorine pentafluoride in tetrachloromethane, T= 0 °C , low ClF5 concentration Boudakian, Max M.; Hyde, Gene A.; Journal of Fluorine Chemistry; vol. 25; (1984); p. 435 - 446 View in Reaxys

Cl Cl

Rx-ID: 3918729 View in Reaxys 24/310 Yield

Conditions & References

6 %, 12 %, With hydrogenchloride, sodium peroxide in acetic acid, Time= 3h, T= 78 - 80 °C 79 % Rudakova, N. I.; Erykalov, Yu. G.; Zharikova, S. M.; Dmitrieva, E. V.; Mataradze, M. S.; Russian Journal of General Chemistry; vol. 65; nb. 2.2; (1995); p. 271 - 272; Zhurnal Obshchei Khimii; vol. 65; nb. 2; (1995); p. 315 - 317 View in Reaxys 79 %, 12 %, 6 %

With hydrogenchloride, sodium peroxide in acetic acid, Time= 3h, T= 78 - 80 °C Rudakova, N. I.; Erykalov, Yu. G.; Zharikova, S. M.; Dmitrieva, E. V.; Mataradze, M. S.; Russian Journal of General Chemistry; vol. 65; nb. 2.2; (1995); p. 271 - 272; Zhurnal Obshchei Khimii; vol. 65; nb. 2; (1995); p. 315 - 317 View in Reaxys

79 %, 6 %, With hydrogenchloride, sodium peroxide in acetic acid, Time= 3h, T= 78 - 80 °C 12 % Rudakova, N. I.; Erykalov, Yu. G.; Zharikova, S. M.; Dmitrieva, E. V.; Mataradze, M. S.; Russian Journal of General Chemistry; vol. 65; nb. 2.2; (1995); p. 271 - 272; Zhurnal Obshchei Khimii; vol. 65; nb. 2; (1995); p. 315 - 317 View in Reaxys With hydrogenchloride, oxygen, aluminum oxide, T= 230 - 300 °C , p= 700.7Torr , Rate constant, Kinetics, Product distribution

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Blanco; Avila; Melo; Bulletin of the Chemical Society of Japan; vol. 56; nb. 3; (1983); p. 909 - 913 View in Reaxys With hydrogenchloride, sodium peroxide in water, acetonitrile, T= 9.85 - 39.85 °C , ΔG(excit.), ΔH(excit.), ΔS(excit.); other solvents, other temperatures, Rate constant, Kinetics, Thermodynamic data Rudakova; Erykalov; Russian Journal of General Chemistry; vol. 67; nb. 11; (1997); p. 1767 - 1769 View in Reaxys H

H 14C H 14C

14C

14CH

H 14C

14CH

H 14C

14C

14CH

Rx-ID: 5197356 View in Reaxys 25/310 Yield 60 %

Conditions & References With iodine, nitric acid, Time= 2h, T= 90 °C , Iodination Robic; Noel; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 42; nb. 2; (1999); p. 109 - 119 View in Reaxys

Cl Cl

Rx-ID: 23402346 View in Reaxys 26/310 Yield 31.67 %Chromat., 9.13 %Chromat., 0.11 %Chromat., 58.98 %Chromat.

Conditions & References 1 :To 150g (1.92 mols) of benzene in a light-shielding reactor were added aluminum chloride 0.09 g (0.675 mmols; 0.35 mmols per mol of benzene) and 10H-phenothiazine-10-carboxylic acid phenyl ester 0.13 g (0.41 mmols; molar ratio of phenothiazine/aluminum chloride is 0.60) at 50°C with stirring. Chlorination was carried out by reacting at the same temperature for 150 minutes with blowing a chlorine gas so as to be a chlorination degree of 1.62 on the basis of benzene. It was confirmed by gas chromatography analysis that the reaction mixture had the following composition. Benzene 0.02percent, chlorobenzene 31.67percent, o-cichlorobenzene 9.13percent, m-dichlorobenzene 0.11percent, p-dichlorobenzene 58.98percent and trichlorobenzene 0.09percent. The para-selectivity calculated based on the above mentioned composition was 86.60percent. With chlorine, AlCl3, aluminium chloride, phenothiazine-10-carboxylic acid phenyl ester, Time= 2.5h, T= 50 °C , Conversion of starting material Patent; Kureha Chemical Industry Co., Ltd.; EP1535890; (2005); (A1) English View in Reaxys

32.15 %Chromat., 9.87 %Chromat., 0.15 %Chromat., 57.67 %Chromat.

2 :To 150g (1.92 mols) of benzene in a light-shielding reactor were added aluminum chloride 0.09g (0.67 mmols; 0.35 mmols per mol of benzene) and 10-chlorocarbonyl-10H-phenothiazine 0.09g (0.34 mmols; molar ratio of phenothiazine/aluminum chloride is 0.50) at 50°C with stirring. Chlorination was carried out by reacting at the same temperature for 170 minutes with blowing a chlorine gas so as to be a chlorination degree of 1.62 on the basis of benzene. It was confirmed by gas chromatography analysis that the reaction mixture had the following composition. Benzene 0.03percent, chlorobenzene 32.15percent, o-cichlorobenzene 9.87percent, m-dichlorobenzene 0.15percent, p-dichlorobenzene 57.67percent and trichlorobenzene 0.13percent. The para-selectivity calculated based on the above mentioned composition was 85.38percent. With chlorine, AlCl3, aluminium chloride, phenothiazine-10-carbonyl chloride, Time= 2.83333h, T= 50 °C , Conversion of starting material Patent; Kureha Chemical Industry Co., Ltd.; EP1535890; (2005); (A1) English View in Reaxys

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F F

Al F F

F F

F F F F F (v3) H F F O– Al Al (v4) (v4) F F F F

F F F

F F

F F F

F F

F F F

P+

Rx-ID: 35442112 View in Reaxys 27/310 Yield 50 %

Conditions & References Stage 1: With Nitrous oxide, Time= 16h, p= 760.051Torr , Schlenk technique Stage 2: in pentane Menard, Gabriel; Hatnean, Jillian A.; Cowley, Hugh J.; Lough, Alan J.; Rawson, Jeremy M.; Stephan, Douglas W.; Journal of the American Chemical Society; vol. 135; nb. 17; (2013); p. 6446 - 6449 View in Reaxys

Rx-ID: 3918652 View in Reaxys 28/310 Yield 7.6 %, 0.7 %

Conditions & References With cobalt (III) fluoride in chloroform, Time= 18h, Heating, other solvents, temperatures, times, Product distribution Zweig, Arnold; Fischer, Robert G.; Lancaster, John E.; Journal of Organic Chemistry; vol. 45; nb. 18; (1980); p. 3597 - 3603 View in Reaxys 1 :Anhydrous AlF3 (ALFAAESAR, 99.5percent) and anhydrous CuF2 (ALFAAESAR, 99.5percent) were used. To a weighed amount of CuF2, AlF3 (35 mesh size) was mixed in different ratios (1:1, 1:1.5, 1:2, 1:2.5, 1:3). In a typical fluorination experiment, the metal fluoride mixture was loaded into a hastelloy reactor tube in a dry box. The reactor tube was heated to 500° C. under a flow of Ar gas. The flow rate of the carrier gas was adjusted to 25 mL/min. Vaporized benzene was passed over the heated fluoride mixture. The duration of the reaction was about 11/2 to 21/2 hrs. At the end of the reaction, the reactor tube was swept out with the carrier gas. The organic product was analyzed using HP 6890 GC/5973 Mass Spectrometer. The inorganic residue was analyzed by powder X-ray diffractometer (XRD PHILIPS APD 3720). Percentage conversions of benzene to the fluorinated products, m-fluorobenzene, flurobenzene, and o-fluorobenzene, where the amount of AlF3 increases and CuF2 remains constant are given in Table 1.; Introducing the benzene in fractions tested the consistency of reactivity of the fluoride bed. The results are given in Table 3. With aluminium trifluoride, CuF2, T= 500 °C , Gas phase, Product distribution / selectivity Patent; University of Florida; US2005/96489; (2005); (A1) English View in Reaxys

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2 :Additional fluorination experiments using other materials such as CaF2, ZnF2, MgF2 and activated carbon as additives were carried out. When benzene was treated with the activated carbon added copper fluoride, no fluorination was observed. The experimental conditions as mentioned in Example 1 were followed and the results are presented in Table 4. With MgF2, T= 500 °C , Gas phase, Product distribution / selectivity Patent; University of Florida; US2005/96489; (2005); (A1) English View in Reaxys

F F O

Rx-ID: 4571466 View in Reaxys 29/310 Yield 36 %, 29 %

Conditions & References With trifluorormethanesulfonic acid, Time= 19h, T= 50 °C Saito, Shinichi; Ohwada, Tomohiko; Shudo, Koichi; Journal of Organic Chemistry; vol. 61; nb. 23; (1996); p. 8089 - 8093 View in Reaxys

29 %, 36 %

With trifluorormethanesulfonic acid, Time= 19h, T= 50 °C Saito, Shinichi; Ohwada, Tomohiko; Shudo, Koichi; Journal of Organic Chemistry; vol. 61; nb. 23; (1996); p. 8089 - 8093 View in Reaxys

I I

tri-iodobenzene

Rx-ID: 28440326 View in Reaxys 30/310 Yield

Conditions & References 1; 5; 6 :In the system shown in FIG. 1, benzene (26.4 g/hr) and iodine (42.9 g/hr) were fed into a reactor without adding monoiodobenzene, and were subjected to a continuous iodination process under conditions of a reaction temperature of 280 °C and atmospheric pressure. 24 hours after the reaction conditions were reached, sampling and analysis were performed. The experimental conditions and results are shown in Table 1 below. With iodine, oxygen, Time= 24 - 400h, T= 280 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2009/54555; (2009); (A1) English View in Reaxys

F F

Rx-ID: 3918648 View in Reaxys 31/310 Yield 27 % Spectr., 7 % Spectr., 18 % Spectr., 33 % Spectr. 33 % Spectr., 7 % Spectr.,

Conditions & References With tetrafluoroammonium tetrafluoroborate in hydrogen fluoride, T= 0 °C , Further byproducts given. Title compound not separated from byproducts Schack, Carl J.; Christe, Karl O.; Journal of Fluorine Chemistry; vol. 18; (1981); p. 363 - 374 View in Reaxys

With tetrafluoroammonium tetrafluoroborate in hydrogen fluoride, T= 0 °C , Further byproducts given. Title compound not separated from byproducts

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18 % Spectr., 27 % Spectr.

Schack, Carl J.; Christe, Karl O.; Journal of Fluorine Chemistry; vol. 18; (1981); p. 363 - 374 View in Reaxys

33 % Spectr., 27 % Spectr., 18 % Spectr., 7 % Spectr.

With tetrafluoroammonium tetrafluoroborate in hydrogen fluoride, T= 0 °C , Further byproducts given. Title compound not separated from byproducts

33 % Spectr., 27 % Spectr., 7% Spectr., 18 % Spectr.

Schack, Carl J.; Christe, Karl O.; Journal of Fluorine Chemistry; vol. 18; (1981); p. 363 - 374 View in Reaxys

With tetrafluoroammonium tetrafluoroborate in hydrogen fluoride, T= 0 °C , Further byproducts given. Title compound not separated from byproducts Schack, Carl J.; Christe, Karl O.; Journal of Fluorine Chemistry; vol. 18; (1981); p. 363 - 374 View in Reaxys

F F

(v2)

Rx-ID: 26403746 View in Reaxys 32/310 Yield

Conditions & References

10.28 %, 0.7 %, 0.3 %

in tetrachloromethane, in presence of a trace of HF; Shaw; Hyman; Journal of the American Chemical Society; vol. 91; (1969); p. 1563 View in Reaxys anonymous; Chemical and Engineering News; vol. 47; nb. Sep. 2; (1969); p. 45 - 45 View in Reaxys vol. He: Edelgasverb.; 1.8.1.2.2, page 29 - 32 ; (from Gmelin) View in Reaxys O

I O O

Rx-ID: 28659627 View in Reaxys 33/310 Yield 21 %, 66 %

Conditions & References With dipotassium peroxodisulfate, sulfuric acid, iodine in 1,2-dichloro-ethane, Time= 20h, T= 40 °C Hossain, Md. Delwar; Kitamura, Tsugio; Bulletin of the Chemical Society of Japan; vol. 80; nb. 11; (2007); p. 2213 - 2219 View in Reaxys

I I

Rx-ID: 848953 View in Reaxys 34/310 Yield

Conditions & References With KIO3, sulfuric acid, iodine Birckenbach; Goubeau; Chemische Berichte; vol. 67; (1934); p. 917,920, 926 View in Reaxys With sulfuric acid, iodine, mercuric sulphate Birckenbach; Goubeau; Chemische Berichte; vol. 67; (1934); p. 917,920, 926 View in Reaxys With sodium peroxodisulphate, iodine, acetic acid

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Elbs; Jaroslawzew; Journal fuer Praktische Chemie (Leipzig); vol. <2> 88; (1913); p. 92 View in Reaxys With mercurous sulphate, sulfuric acid, iodine Birckenbach; Goubeau; Chemische Berichte; vol. 67; (1934); p. 917,920, 926 View in Reaxys 72 %Chro- With cerium (IV) oxide, dihydrogen peroxide, iodine in water, Time= 10h, pH= 3, Reflux mat., 4 %Chromat. Zhang, Peng; Sun, Dongqing; Wen, Mingwei; Yang, Jingkui; Zhou, Kebin; Wang, Zhixiang; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 720 - 729 View in Reaxys 2H 2H

2H 2H

Rx-ID: 2012285 View in Reaxys 35/310 Yield

Conditions & References

With antimony(V) pentachloride, Time= 1h, Ambient temperature Lau, W.; Kochi, J. K.; Journal of the American Chemical Society; vol. 108; nb. 21; (1986); p. 6720 - 6732 View in Reaxys H

H 13C H 13C

13C

13CH

H 13C

13CH

H 13C

13C

13CH

Rx-ID: 2130944 View in Reaxys 36/310 Yield 35 %

Conditions & References With iodine, nitric acid, Time= 1.5h, Heating McCurry; Daves Jr.; Analytical Chemistry; vol. 58; nb. 13; (1986); p. 2785 - 2788 View in Reaxys

Rx-ID: 3918728 View in Reaxys 37/310 Yield 5.4 %, 3.9 %, 5.2 %, 12.7 %

Conditions & References With chlorine pentafluoride in tetrachloromethane, T= 0 °C , high ClF5 concentration Boudakian, Max M.; Hyde, Gene A.; Journal of Fluorine Chemistry; vol. 25; (1984); p. 435 - 446 View in Reaxys Cl Cl

Rx-ID: 3918732 View in Reaxys 38/310 Yield

Conditions & References With chlorine, zeolite NaHZSM-5, T= 170 - 180 °C , Yield given. Further byproducts given. Yields of byproduct given Huizinga; Scholten; Wortel; van Bekkum; Tetrahedron Letters; vol. 21; nb. 39; (1980); p. 3809 - 3812 View in Reaxys With chlorine, zeolite REY (SK-500), T= 170 - 180 °C , Yield given. Yields of byproduct given

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Huizinga; Scholten; Wortel; van Bekkum; Tetrahedron Letters; vol. 21; nb. 39; (1980); p. 3809 - 3812 View in Reaxys

Br Br

Rx-ID: 3918776 View in Reaxys 39/310 Yield

Conditions & References With oxygen, potassium bromide, sodium nitrite in water, trifluoroacetic acid, Time= 24h, T= 20 °C , Product distribution Cheprakov, A. V.; Makhon'kov, D. I.; Rodkin, M. A.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 2; (1988); p. 217 - 223; Zhurnal Organicheskoi Khimii; vol. 24; nb. 2; (1988); p. 248 255 View in Reaxys With hydrogen bromide, oxygen, ruthenium trichloride, Time= 17h, T= 145 °C , p= 750.075Torr Limberg, Christian; Teles, Joaquim Henrique; Advanced Synthesis and Catalysis; vol. 343; nb. 5; (2001); p. 447 449 View in Reaxys

131I

Rx-ID: 5247754 View in Reaxys 40/310 Yield

Conditions & References With N-chloro-succinimide, [131I]-sodium iodide, Time= 2h, T= 20 °C , Iodination Mennicke; Holschbach; Coenen; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 42; nb. SUPPL. 1; (1999); p. S801-S803 View in Reaxys With lead(IV) acetate, iodide anion in trifluoroacetic acid, Time= 0.166667h, Iodination Mennicke; Holschbach; Coenen; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 42; nb. SUPPL. 1; (1999); p. S294-S296 View in Reaxys With N-chloro-succinimide, [131I]-sodium iodide, trifluorormethanesulfonic acid, Time= 0.25h, T= 20 °C , Iodination Mennicke; Holschbach; Coenen; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 43; nb. 7; (2000); p. 721 - 737 View in Reaxys

HO O

Cl Cl

Tetrachlorinated benzenes; mixture of Cl

Rx-ID: 8765222 View in Reaxys 41/310 Yield

Conditions & References With potassium chloride, oxygen, calcium chloride, aluminium trichloride, iron(III) chloride, T= 400 °C , Formation of xenobiotics, Further byproducts given. Title compound not separated from byproducts Sidhu, Sukh; Kasti, Nabil; Edwards, Phil; Dellinger, Barry; Chemosphere; vol. 42; nb. 5-7; (2001); p. 499 - 506

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View in Reaxys

F N F

Rx-ID: 31774360 View in Reaxys 42/310 Yield

Conditions & References With nitrogen trifluoride, T= 400 - 410 °C , p= 760.051Torr , Gas phase Belter, Randolph K.; Journal of Fluorine Chemistry; vol. 132; nb. 11; (2011); p. 961 - 964 View in Reaxys

Rx-ID: 847611 View in Reaxys 43/310 Yield

Conditions & References With aluminium trichloride Sherrill; Journal of the American Chemical Society; vol. 46; (1924); p. 2756 View in Reaxys 2H

2H 2H

Rx-ID: 2012286 View in Reaxys 44/310 Yield 20 %, 3 %

Conditions & References With bromine in pyridine Sbrana, G.; Neto, N.; Muniz-Miranda, M.; Nocentini, M.; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 39; nb. 4; (1983); p. 295 - 304 View in Reaxys Cl Cl

Cl Cl

Rx-ID: 3918733 View in Reaxys 45/310 Yield

I 3H

3H 3H

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-1 F

(v4)

I 3H

B FF

3H 3H

I+

3H 3H

Rx-ID: 5261035 View in Reaxys 46/310 Yield

Conditions & References

52 %, 27 With potassium tetrafluoroborate, Time= 240h, T= 5 - 25 °C , Radiolysis, Arylation, Further byproducts given %, 18 %, 7 Shchepina; Nefedov; Toropova; Avrorin; Lewis, Scott B.; Mattson, Bruce; Tetrahedron Letters; vol. 41; nb. 1; % (2000); p. 25 - 27 View in Reaxys

Rx-ID: 30200268 View in Reaxys 47/310 Yield

Conditions & References Stage 1: With Au2Cl6H2 in hexane, Time= 0.5h, T= 20 °C , Inert atmosphere Stage 2: With 2,6-dimethylpyridine in diethyl ether, Inert atmosphere Stage 3: With N-Benzylbenzylamine in tetrahydrofuran, Time= 24h, T= 70 °C , Inert atmosphere Lavy, Severine; Miller, Jeremie J.; Pazicky, Marek; Rodrigues, Anne-Sophie; Rominger, Frank; Jaekel, Christoph; Serra, Daniel; Vinokurov, Nikolai; Limbach, Michael; Advanced Synthesis and Catalysis; vol. 352; nb. 17; (2010); p. 2993 - 3000 View in Reaxys

Cl Cl

Rx-ID: 35285544 View in Reaxys 48/310 Yield

Conditions & References With dipotassium peroxodisulfate, sodium chloride in acetonitrile-D3, water, Time= 1h, T= 100 °C , regioselective reaction Gu, Liuqun; Lu, Ting; Zhang, Mingyun; Tou, Lijuan; Zhang, Yugen; Advanced Synthesis and Catalysis; vol. 355; nb. 6; (2013); p. 1077 - 1082 View in Reaxys F

2H 2H

C–

(v4) (v5)

Ir3+ – SP-5 N (v4)N – (v3) N N

(v3)

(v4)

2H 2H

(v4)

C–

(v5) NIr3+ – SP-5 N (v4) (v3) (v3) N (v4)

(v4)

C–

(v5) Ir3+ – N SP-5 N – (v4) N(v4) N (v3) (v3)

N–

Rx-ID: 40118757 View in Reaxys 49/310 Yield

Conditions & References

12 %, 7 %, With potassium hydroxide in neat (no solvent), Time= 96h, T= 200 °C , Inert atmosphere 16 Li, Bao Zhu; Qian, Ying Ying; Liu, Jianwen; Chan, Kin Shing; Organometallics; vol. 33; nb. 24; (2014); p. 7059 %Spectr. 7068

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View in Reaxys

O O

O HO

Rx-ID: 3918638 View in Reaxys 50/310 Yield

Conditions & References With iodine in benzene, Time= 33h, T= 79 °C , Yield given Correa, Carlos M. M. da Silva; Oliveira, Maria Augusta B. C. S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 711 - 716 View in Reaxys With iodine in benzene, Time= 13h, Heating, Yield given Correa, Carlos M. M. da Silva; Oliveira, Maria Augusta B. C. S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 711 - 716 View in Reaxys

Cl I

Rx-ID: 3918727 View in Reaxys 51/310 Yield

Conditions & References

80 %

With aluminium trichloride, bis-[(trifluoroacetoxy)iodo]benzene, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys

Rx-ID: 4032827 View in Reaxys 52/310 Yield

Conditions & References

80 %

With fluorine, T= 296 °C , p= 1.5Torr , Irradiation, different initial F atom concentrations, ΔH(excit.), Rate constant, Product distribution, Thermodynamic data Ebrecht, J.; Hack, W.; Wagner, H. Gg.; Berichte der Bunsen-Gesellschaft; vol. 93; (1989); p. 619 - 626 View in Reaxys

Bi5+ C– 3

2 Br–

Rx-ID: 26090366 View in Reaxys 53/310 Yield 99 %

Conditions & References in toluene, solvent removing, crystals washing and drying Sharutin, V. V.; Sharutina, O. K.; Egorova, I. V.; Panova, L. P.; Russian Journal of General Chemistry; vol. 68; (1998); p. 318 - 319; Zhurnal Obshchei Khimii; vol. 68; (1998); p. 345 - 346 ; (from Gmelin) View in Reaxys

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–C

O–

I O–

Tl3+

Tl+

(v0)

Tl3+

Rx-ID: 27229274 View in Reaxys 54/310 Yield

Conditions & References

100 %, 99 %

in acetonitrile, soln. of iodine addn. to soln. of Tl-compd., mixing, standing (dark, 220h, room temperature), evacuation (under Ar, room temperature, then wate r bath, distillation of I-compd.), product remaining in solid residue Gun'kin, I. F.; Russian Journal of General Chemistry; vol. 65; nb. 3.2; (1995); p. 460; Zhurnal Obshchei Khimii; vol. 65; nb. 3; (1995); p. 518 ; (from Gmelin) View in Reaxys

2H 2H

Br 2H

2H 2H

Rx-ID: 29400669 View in Reaxys 55/310 Yield

Conditions & References

37.6 With gold(III) chloride, N-bromosuccinmide in dichloromethane, Time= 8h, T= 80 °C , Inert atmosphere %Chromat., 62.4 Mo, Fanyang; Yan, Jerry Mingtao; Qiu, Di; Li, Fei; Zhang, Yan; Wang, Jianbo; Angewandte Chemie - Interna%Chromat. tional Edition; vol. 49; nb. 11; (2010); p. 2028 - 2032 View in Reaxys

F F O

Rx-ID: 4571467 View in Reaxys 56/310 Yield

Conditions & References

8 %, 11 %, 69 mg, 2 %

With trifluorormethanesulfonic acid, Time= 5h, T= 50 °C Saito, Shinichi; Ohwada, Tomohiko; Shudo, Koichi; Journal of Organic Chemistry; vol. 61; nb. 23; (1996); p. 8089 - 8093 View in Reaxys

Rx-ID: 5082428 View in Reaxys 57/310 Yield

Conditions & References With dibenzoyl peroxide, Time= 24h, Heating, deiodination Dolenc, Darko; Plesnicar, Bozo; Journal of the American Chemical Society; vol. 119; nb. 11; (1997); p. 2628 2632 View in Reaxys 3H 3H

Br 3H

3H 3H

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-1 F

(v4)

Br 3H

B FF

3H 3H

Br+

3H 3H

Rx-ID: 5259441 View in Reaxys 58/310 Yield

Conditions & References

27 %, 11 %, 9 %, 7 %

With potassium tetrafluoroborate, Time= 240h, T= 5 - 25 °C , Radiolysis, Arylation, Further byproducts given Shchepina; Nefedov; Toropova; Avrorin; Lewis, Scott B.; Mattson, Bruce; Tetrahedron Letters; vol. 41; nb. 1; (2000); p. 25 - 27 View in Reaxys 3H 3H

I 3H

3H 3H

-1 F

(v4)

I F

I 3H

B FF

3H 3

I+

H 3H

Rx-ID: 5261036 View in Reaxys 59/310 Yield

Conditions & References

27 %, 4 %, With potassium tetrafluoroborate, Time= 240h, T= 5 - 25 °C , Radiolysis, Arylation, Further byproducts given 52 %, 4 % Shchepina; Nefedov; Toropova; Avrorin; Lewis, Scott B.; Mattson, Bruce; Tetrahedron Letters; vol. 41; nb. 1; (2000); p. 25 - 27 View in Reaxys

2 Br–

C–

Sb5+

Br Sb

Rx-ID: 26672082 View in Reaxys 60/310 Yield

Conditions & References

86 %, 96 %

in toluene, 0.5 h, 20°C; solvent and bromobenzene removing, crystals washing (petroleum ether) and drying, Ph4SbBr in residue, Ph3Bi in petroleum ether soln. Sharutin, V. V.; Sharutina, O. K.; Egorova, I. V.; Panova, L. P.; Russian Journal of General Chemistry; vol. 68; (1998); p. 318 - 319; Zhurnal Obshchei Khimii; vol. 68; (1998); p. 345 - 346 ; (from Gmelin) View in Reaxys

F F

F O

O F

Rx-ID: 3917071 View in Reaxys 61/310 Yield 39 % Chromat., 2 % Chromat., 2 % Chromat.

Conditions & References in dichloromethane, T= 0 °C , Title compound not separated from byproducts Fifolt, Michael J.; Olczak, Raymond T.; Mundhenke, Rudolph F.; Journal of Organic Chemistry; vol. 50; nb. 23; (1985); p. 4576 - 4582 View in Reaxys

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O O

I N

N O

Rx-ID: 3917501 View in Reaxys 62/310 Yield

Conditions & References

71 %

With copper acetylacetonate in benzene, Time= 1h, T= 6 °C , influence of temperature and reagents on the decomposition time of phenyliodonium dinitromethylide, Product distribution Semenov, V. V.; Bruskin, A. B.; Shevelev, S. A.; Fainzil'berg, A. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; nb. 12; (1982); p. 2423 - 2427; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1982); p. 2741 - 2746 View in Reaxys

F F

Rx-ID: 4209222 View in Reaxys 63/310 Yield

Conditions & References

79.4 % Chromat., 10.1 % Chromat.

With nitrogen, fluorine, trifluoroacetic acid in monofluoro-trichloromethane, T= -30 °C , different educt and reagent concentration, different temperatures, different fluorine/nitrogen ratio, different solvents, without or with different additives, Product distribution Conte, L.; Gambaretto, G. P.; Napoli, M.; Fraccaro, C.; Legnaro, E.; Journal of Fluorine Chemistry; vol. 70; nb. 2; (1995); p. 175 - 180 View in Reaxys 3.1 With 1-fluoro-2,4,6-trichloro-1,3,5-triazinium tetrafluoroborate, T= 20 - 60 °C , Product distribution / selectivity Patent; AIR PRODUCTS AND CHEMICALS, INC.; EP1201627; (2002); (A1) English View in Reaxys 20.2 With 1-fluoro-2,4,6-trichloro-1,3,5-triazinium tetrafluoroborate in nitromethane, Time= 2h, T= 20 - 70 °C , Product distribution / selectivity Patent; AIR PRODUCTS AND CHEMICALS, INC.; EP1201628; (2002); (A1) English View in Reaxys 5.2 With 1-fluoro-2,4,6-trichloro-1,3,5-triazinium tetrafluoroborate in nitromethane, Time= 2h, T= 20 - 70 °C , Product distribution / selectivity Patent; AIR PRODUCTS AND CHEMICALS, INC.; EP1201627; (2002); (A1) English View in Reaxys 3.1 With 1-fluoro-2,4,6-trichloro-1,3,5-triazinium tetrafluoroborate, T= 20 - 60 °C , Product distribution / selectivity Patent; AIR PRODUCTS AND CHEMICALS, INC.; EP1201628; (2002); (A1) English View in Reaxys H

H 14C H 14C

14C

H 14C

CH CH

14C

14CH

Rx-ID: 4823052 View in Reaxys 64/310

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Yield

Conditions & References With KBrO3, sulfuric acid, acetic acid in water, Ambient temperature Szammer; Simon-Trompler; Mate; Abermann; Uermoes; Klebovich; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 39; nb. 12; (1997); p. 1011 - 1018 View in Reaxys

Rx-ID: 5082422 View in Reaxys 65/310 Yield

Conditions & References in water, Time= 0.5h, T= 3 °C , sonication, Elimination Kruus, Peeter; Beutel, Lise; Aranda, Rocio; Penchuk, Jaan; Otson, Rein; Chemosphere; vol. 36; nb. 8; (1998); p. 1811 - 1824 View in Reaxys

HNO3+H2SO4

dimethoxycarbonyl-β-resorcylic acid-chloride

Rx-ID: 19265065 View in Reaxys 66/310 Yield

Conditions & References Reaction Steps: 2 1: 89 percent / triflic acid / 1,1,2-trichloro-1,2,2-trifluoro-ethane / 24 h / 0 °C 2: 89 percent / 140 - 145 °C With trifluorormethanesulfonic acid in 1,2,2-trifluoro-trichloroethane Unemoto, Teruo; Gotoh, Yoshihiko; Journal of Fluorine Chemistry; vol. 28; (1985); p. 235 - 240 View in Reaxys

Bi5+ 2 Cl –

C–

Rx-ID: 26090367 View in Reaxys 67/310 Yield 74 %, 79 %

Conditions & References in toluene, 0.5 h at 20°C; solvent and chlorobenzene removing, resulting crystals washing (petroleum ether), drying Sharutin, V. V.; Sharutina, O. K.; Egorova, I. V.; Panova, L. P.; Russian Journal of General Chemistry; vol. 68; (1998); p. 318 - 319; Zhurnal Obshchei Khimii; vol. 68; (1998); p. 345 - 346 ; (from Gmelin) View in Reaxys F F

(v5) (v5)H (v5)H H (v5) C – H H (v4) Zr 2+ (v12) (v5) H – H CH H (v5) H (v4) (v5)(v5)

(v4) (v5) (v5) (v5) (v5) (v5)

(v5)

H C–

(v4) C– Zr 4+ (v4) – (v12) C

C– (v5) H (v5)

C+

F F

F F B–

F F

(v4)

F F F F

F F

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–HC

1.5 F

C–

F F F F

Zr 4+

B–

F F

Rx-ID: 27579718 View in Reaxys 68/310 Yield 43 %

Conditions & References in further solvent(s), byproducts: Ph3CMe; (N2); drybox or Schlenk technique; soln. of Zr-aryl complex (1 equiv.) and Zr-methyl complex (1 equiv.) in C6H5Cl was added dropwise to soln. ofB compd. (2 equiv.) in dark; stirred at 23°C for 30 min; volatiles removed (vac.); washed (C6H6); dried (vac.) Sydora, Orson L.; Kilyanek, Stefan M.; Jordan, Richard F.; Organometallics; vol. 26; nb. 19; (2007); p. 4746 4755 ; (from Gmelin) View in Reaxys

F F

T-4

F F

Rx-ID: 3918649 View in Reaxys 69/310 Yield 47 %, 2.3 %, 1.9 %, 4.1 %, 6.3 %, 7.4 %

Conditions & References With silver(II) fluoride in hexane, Time= 0.2h, T= 40 °C , other solvents, times, temperatures, ratios, Product distribution, Mechanism Zweig, Arnold; Fischer, Robert G.; Lancaster, John E.; Journal of Organic Chemistry; vol. 45; nb. 18; (1980); p. 3597 - 3603 View in Reaxys

F F

Rx-ID: 3918651 View in Reaxys 70/310 Yield

Conditions & References

6 %, 20 %, With hydrogen fluoride, triethylamine, anodic oxidation 4 %, 18 % Meurs, Jan H. H.; Sopher, David W.; Eilenberg, Wolf; Angewandte Chemie; vol. 101; nb. 7; (1989); p. 955 - 956 View in Reaxys 18 %, 20 %, 4 %, 6 %

With hydrogen fluoride, triethylamine, anodic oxidation Meurs, Jan H. H.; Sopher, David W.; Eilenberg, Wolf; Angewandte Chemie; vol. 101; nb. 7; (1989); p. 955 - 956 View in Reaxys

18 %, 6 %, With hydrogen fluoride, triethylamine, anodic oxidation 20 %, 4 % Meurs, Jan H. H.; Sopher, David W.; Eilenberg, Wolf; Angewandte Chemie; vol. 101; nb. 7; (1989); p. 955 - 956 View in Reaxys 18 %, 6 %, With hydrogen fluoride, triethylamine, anodic oxidation 4 %, 20 % Meurs, Jan H. H.; Sopher, David W.; Eilenberg, Wolf; Angewandte Chemie; vol. 101; nb. 7; (1989); p. 955 - 956 View in Reaxys With pyridine*49HF, electrolysis

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Meurs; Eilenberg; Tetrahedron; vol. 47; nb. 4-5; (1991); p. 705 - 714 View in Reaxys With pyridine-hydrogen fluoride (1:4) complex, electrolysis Meurs; Eilenberg; Tetrahedron; vol. 47; nb. 4-5; (1991); p. 705 - 714 View in Reaxys 3H 3H

Br 3H

3H 3H

-1 F

(v4)

Br F

Br 3H

B FF

3H 3H

Br+

H 3H

Rx-ID: 5259442 View in Reaxys 71/310 Yield

Conditions & References

11 %, 27 %, 9 %, 4 %

3H 3H

Cl 3H

Rx-ID: 5283144 View in Reaxys 72/310 Yield

Conditions & References

12 %, 10 %, 11 %, 5 %

3H 3H

-1 F

3H 3H

(v4)

Cl 3H

B FF

3H 3H

Cl +

3H 3H

Rx-ID: 5283145 View in Reaxys 73/310 Yield

Conditions & References

10 %, 8 %, With potassium tetrafluoroborate, Time= 240h, T= 5 - 25 °C , Radiolysis, Arylation, Further byproducts given 11 %, 12 % Shchepina; Nefedov; Toropova; Avrorin; Lewis, Scott B.; Mattson, Bruce; Tetrahedron Letters; vol. 41; nb. 1; (2000); p. 25 - 27 View in Reaxys

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Cl Cl

dichloro-benzene, trichloro-benzene Cl

Rx-ID: 6212791 View in Reaxys 74/310 Yield

Conditions & References With hydrogenchloride, iron(III) chloride, T= 200 °C Patent; C. H. Boehringer Sohn; US2880246; (1955) View in Reaxys With hydrogenchloride, antimony(V) pentachloride, T= 200 °C Patent; C. H. Boehringer Sohn; US2880246; (1955) View in Reaxys

dipyridine-iodo(I)-perchlorate Rx-ID: 6585470 View in Reaxys 75/310 Yield

Conditions & References With trichloroacetic acid, T= 20 °C Patent; Carlsohn; DE692324; (1930); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 25; p. 126 View in Reaxys

diiodobenzene; triiodobenzene Rx-ID: 6727889 View in Reaxys 76/310 Yield

Conditions & References With iodine, iodic acid, T= 200 - 240 °C Kekule; Justus Liebigs Annalen der Chemie; vol. 137; (1866); p. 167 View in Reaxys

Cl Br

Rx-ID: 32101527 View in Reaxys 77/310 Yield

Conditions & References With bromine, Time= 4h, T= 100 °C , Reflux, Ionic liquid Shi, Shen Yi; Kong, Ai Guo; Zhao, Xin Hua; Ding, Han Ming; Yang, Fan; Shan, Yong Kui; Chinese Chemical Letters; vol. 22; nb. 2; (2011); p. 147 - 150 View in Reaxys

F F

O F

Rx-ID: 3918650 View in Reaxys 78/310 Yield

Conditions & References With trifluoromethyl hypofluorite in dichloromethane, T= 0 °C , other sub. aromatic hydrocarbons and anilines; other solvents and temp., Product distribution

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Fifolt, Michael J.; Olczak, Raymond T.; Mundhenke, Rudolph F.; Journal of Organic Chemistry; vol. 50; nb. 23; (1985); p. 4576 - 4582 View in Reaxys 2 % Chromat., 2 % Chromat., 39 % Chromat.

With trifluoromethyl hypofluorite in dichloromethane, T= 0 °C , Title compound not separated from byproducts

39 % Chromat., 2 % Chromat., 2 % Chromat.

With trifluoromethyl hypofluorite in dichloromethane, T= 0 °C , Title compound not separated from byproducts

Fifolt, Michael J.; Olczak, Raymond T.; Mundhenke, Rudolph F.; Journal of Organic Chemistry; vol. 50; nb. 23; (1985); p. 4576 - 4582 View in Reaxys

O N O

Rx-ID: 3918716 View in Reaxys 79/310 Yield

Conditions & References

100 %

With potassium chloride, potassium nitrate, trifluoroacetic acid, Time= 5.04h, T= 20 °C , other time, other ratio of reagents, other solvent, Product distribution, Mechanism Makhon'kov, D. I.; Cheprakov, A. V.; Rodkin, M. A.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 2; (1988); p. 211 - 217; Zhurnal Organicheskoi Khimii; vol. 24; nb. 2; (1988); p. 241 248 View in Reaxys

I HO

Rx-ID: 32869203 View in Reaxys 80/310 Yield

Conditions & References

12 %Chro- With cerium (IV) oxide, dihydrogen peroxide, iodine in water, pH= 4.5, Reflux mat., 7 %Chromat. Zhang, Peng; Sun, Dongqing; Wen, Mingwei; Yang, Jingkui; Zhou, Kebin; Wang, Zhixiang; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 720 - 729 View in Reaxys

Cl Cl

Rx-ID: 3918734 View in Reaxys 81/310 Yield

Conditions & References With chlorine, L type zeolite (TSZ-500KOA) in 1,2-dichloro-ethane, Time= 3h, T= 70 °C , var. solvents, also reaction in the presence of oxygen, Product distribution Nakamura, Tadashi; Shinoda, Kiyonori; Yasuda, Kensei; Chemistry Letters; nb. 10; (1992); p. 1881 - 1882 View in Reaxys

–O

F Pb4+

B F

F O

Rx-ID: 26143869 View in Reaxys 82/310

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Yield

Conditions & References

39 %

With mercury(II) diacetate, Stirring of benzene in BF3*Et2O contg. Pb(OAc)4 and overnight at room temp.; GC anal. 42percent recovery of benzene. Meio, Giuseppe V. De; Pinhey, John T.; Journal of the Chemical Society, Chemical Communications; nb. 15; (1990); p. 1065 - 1066 ; (from Gmelin) View in Reaxys

5 C– 2

Cr 3+

Li+

Rx-ID: 26621647 View in Reaxys 83/310 Yield

Conditions & References With iodine Hein, F.; Weiss, R.; Naturwissenschaften; vol. 46; (1959); p. 321 - 322 ; (from Gmelin) View in Reaxys With I2 vol. Cr: Org.Verb.; 1.1.1.2.8, page 22 - 23 ; (from Gmelin) View in Reaxys

I Cr

C–

2 Na +

Cr 3+

(v3)

Rx-ID: 26621650 View in Reaxys 84/310 Yield

Conditions & References With iodine, byproducts: NaI Hein, F.; Weiss, R.; Naturwissenschaften; vol. 46; (1959); p. 321 - 322 ; (from Gmelin) View in Reaxys With I2, byproducts: NaI Hein, F.; Schmiedeknecht, K.; Journal of Organometallic Chemistry; vol. 5; (1966); p. 454 - 462 View in Reaxys vol. Cr: Org.Verb.; 1.1.1.2.8, page 22 - 23 ; (from Gmelin) View in Reaxys 2H

O O

I O

2H 2H

Rx-ID: 39631382 View in Reaxys 85/310 Yield

Conditions & References With pyridine, tetradeuterioacetic acid, palladium diacetate, T= 100 °C , Reagent/catalyst Cook, Amanda K.; Sanford, Melanie S.; Journal of the American Chemical Society; vol. 137; nb. 8; (2015); p. 3109 - 3118 View in Reaxys

Br Br

Cl Br

Br HO

Rx-ID: 848507 View in Reaxys 86/310

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Yield

Conditions & References With aluminium trichloride Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

Br Cl

Br HO

Rx-ID: 848523 View in Reaxys 87/310 Yield

Conditions & References With aluminium trichloride Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

S O

Rx-ID: 3933536 View in Reaxys 88/310 Yield

Conditions & References With other solvents in 1,2,2-trifluoro-trichloroethane, T= 24.9 °C , Rate constant Chatgilialoglu, C.; Journal of Organic Chemistry; vol. 51; nb. 15; (1986); p. 2871 - 2873 View in Reaxys

sulfur

m-toluic acid phenyl ester Rx-ID: 18337081 View in Reaxys 89/310

Yield

Conditions & References Reaction Steps: 2 1: 89 percent / various solvent(s) / 24 h / 0 °C 2: 89 percent / 140 - 145 °C in various solvent(s) Umemoto, Teruo; Gotoh, Yoshihiko; Bulletin of the Chemical Society of Japan; vol. 60; nb. 9; (1987); p. 3307 3314 View in Reaxys Cl Cl

Cl Cl

Rx-ID: 30946541 View in Reaxys 90/310 Yield 15 %, 10 %

Conditions & References With chlorine, Time= 6h Ivanov; Tsentalovich; Kogan; Tomilova; Zefirov; Russian Chemical Bulletin; vol. 57; nb. 8; (2008); p. 1676 - 1679 View in Reaxys

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Rx-ID: 847492 View in Reaxys 91/310 Yield

Conditions & References langsame Neutronen.Irradiation Glueckauf; Fay; Journal of the Chemical Society; (1936); p. 392 View in Reaxys T= 150 - 180 °C Hunter; Edgar; Journal of the American Chemical Society; vol. 54; (1932); p. 2025,2026 View in Reaxys

F F

1.)Nafion H

O F F

Rx-ID: 6585462 View in Reaxys 92/310 Yield

Conditions & References With propane-1-thiol, 1.)in trifluoroacetic acid-trifluoroacetic anhidrid, 0 deg C, 6 h, then at room temp., 4 d,, Yield given. Multistep reaction Umemoto, Teruo; Tetrahedron Letters; vol. 25; nb. 1; (1984); p. 81 - 82 View in Reaxys

F 2H

H 2

Rx-ID: 10198158 View in Reaxys 93/310 Yield

Conditions & References With 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) in acetonitrile-D3, T= 110 °C , Product distribution, Further Variations: Reaction partners, Reagents, Solvents, Temperatures Borodkin, Gennady I.; Zaikin, Pavel A.; Shubin, Vyacheslav G.; Tetrahedron Letters; vol. 47; nb. 15; (2006); p. 2639 - 2642 View in Reaxys With 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) in acetonitrile, T= 110 °C Borodkin; Zaikin; Shakirov; Shubin; Russian Journal of Organic Chemistry; vol. 43; nb. 10; (2007); p. 1451 - 1459 View in Reaxys

Rx-ID: 26143931 View in Reaxys 94/310 Yield

Conditions & References in neat (no solvent) Sconce, J. S.; Chlorine. Its Manufacture, Properties and Uses, New York 1962, S. 39 View in Reaxys Sconce, J. S.; Chlorine. Its Manufacture, Properties and Uses, New York 1962, S. 42 ; (from Gmelin) View in Reaxys vol. Cl: SVol.A; 158, page 373 - 375 ; (from Gmelin)

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View in Reaxys

Cl Cl Cl

Rx-ID: 847597 View in Reaxys 95/310 Yield

Conditions & References With aluminium trichloride Prins; Journal fuer Praktische Chemie (Leipzig); vol. <2>89; (1914); p. 416 View in Reaxys Mouneyrat; Bulletin de la Societe Chimique de France; vol. <3> 19; (1898); p. 555 View in Reaxys

Rx-ID: 3918684 View in Reaxys 96/310 Yield

Conditions & References

48.6 % Chromat.

With At(1+) in acetic acid, Time= 1.5h, T= 120 °C , further temperatures and periods of time, Product distribution Vasharosh, L.; Norseev, Yu. V.; Khalkin, V. A.; Doklady Chemistry; vol. 266; (1982); p. 297 - 299; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 266; nb. 1; (1982); p. 120 - 122 View in Reaxys Cl Cl Cl

Cl Cl

Rx-ID: 3918730 View in Reaxys 97/310 Yield

Conditions & References With chlorine, zeolite REY (SK-500), T= 170 - 180 °C , Yield given. Yields of byproduct given Huizinga; Scholten; Wortel; van Bekkum; Tetrahedron Letters; vol. 21; nb. 39; (1980); p. 3809 - 3812 View in Reaxys With chlorine, zeolite NaHZSM-5, T= 170 - 180 °C , variation of catalysts, Product distribution Huizinga; Scholten; Wortel; van Bekkum; Tetrahedron Letters; vol. 21; nb. 39; (1980); p. 3809 - 3812 View in Reaxys

Rx-ID: 4032774 View in Reaxys 98/310 Yield 36.3 % Chromat., 9.9 % Chromat., 17.9 % Chromat. 17.9 % Chromat., 9.9 %

Conditions & References Time= 20h, T= 25 °C , Irradiation Nakada; Miura; Nishiyama; Higashi; Mori; Hirota; Ishii; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3122 - 3126 View in Reaxys

Time= 20h, T= 25 °C , Irradiation

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Chromat., 36.3 % Chromat.

Nakada; Miura; Nishiyama; Higashi; Mori; Hirota; Ishii; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3122 - 3126 View in Reaxys

Br 2H

Rx-ID: 4032781 View in Reaxys 99/310 Yield 20.3 % Chromat., 4 % Chromat., 8.6 % Chromat. 8.6 % Chromat., 4.0 % Chromat., 20.3 % Chromat.

Conditions & References Time= 15h, T= 25 °C , Irradiation Nakada; Miura; Nishiyama; Higashi; Mori; Hirota; Ishii; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3122 - 3126 View in Reaxys

Time= 15h, T= 25 °C , Irradiation Nakada; Miura; Nishiyama; Higashi; Mori; Hirota; Ishii; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3122 - 3126 View in Reaxys

di-, tri-, tetra- and pentachlorobenzenes Rx-ID: 6727710 View in Reaxys 100/310 Yield

Conditions & References With chlorine, carbon, Time= 3h, T= 25 °C , other carbons, Product distribution Puri, Balwant Rai; Singh, D. D.; Kaura, N. C.; Verma, S. K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical; vol. 19; nb. 2; (1980); p. 109 - 112 View in Reaxys

diphenylmono and -diselenide Rx-ID: 6728058 View in Reaxys 101/310 Yield

Conditions & References With carbon disulfide, aluminum tri-bromide, selenium(II) bromide Loevenich; Sipmann; Journal fuer Praktische Chemie (Leipzig); vol. <2> 124; (1929); p. 132 View in Reaxys

chloronaphthalenes; mixture of Cl

Rx-ID: 8797657 View in Reaxys 102/310 Yield

Conditions & References With oxygen, Formation of xenobiotics, combustion, Title compound not separated from byproducts Burfeindt; Homann; Chemosphere; vol. 42; nb. 5-7; (2001); p. 439 - 447

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View in Reaxys

H B

Rx-ID: 26418783 View in Reaxys 103/310 Yield

Conditions & References in benzene, under ice-cooling; Allenstein, E.; Goubeau, J.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 322; (1963); p. 145 - 154 ; (from Gmelin) View in Reaxys in benzene, under ice-cooling; vol. Cl: SVol.B2; 76, page 485 - 487 ; (from Gmelin) View in Reaxys

Rx-ID: 632086 View in Reaxys 104/310 Yield

Conditions & References With iron(III) chloride Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys

O O

Rx-ID: 786612 View in Reaxys 105/310 Yield

Conditions & References With carbon disulfide, aluminium trichloride Olivier; Recueil des Travaux Chimiques des Pays-Bas; vol. 33; (1914); p. 130,152; Chem. Zentralbl.; vol. 85; nb. I; (1914); p. 2166 View in Reaxys

Rx-ID: 846740 View in Reaxys 106/310 Yield

Conditions & References With iron(III) chloride Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys

I N

Rx-ID: 847117 View in Reaxys 107/310 Yield

Conditions & References With aluminium trichloride

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Woolf; Journal of the Chemical Society; (1954); p. 252,253, 257, 258 View in Reaxys

Br HO

Br Br

Rx-ID: 848505 View in Reaxys 108/310 Yield

Conditions & References With aluminium trichloride Kohn; Mueller; Monatshefte fuer Chemie; vol. 30; (1909); p. 407 View in Reaxys

Br Br

Rx-ID: 848945 View in Reaxys 109/310 Yield

Conditions & References With bromine, carbon Nikolajew; Zhurnal Obshchei Khimii; vol. 1; (1931); p. 1035; Chem. Zentralbl.; vol. 104; nb. I; (1933); p. 1428 View in Reaxys O Cl

Cl O

Rx-ID: 849123 View in Reaxys 110/310 Yield

Conditions & References With chlorine dioxide Carius; Justus Liebigs Annalen der Chemie; vol. 143; (1867); p. 316 View in Reaxys

O N O

Rx-ID: 3918713 View in Reaxys 111/310 Yield 94 % Chromat., 6 % Chromat.

Conditions & References With ammonium nitrate, potassium iodide in trifluoroacetic acid, Time= 0.5h, T= 20 °C , Product distribution Makhon'kov, D. I.; Cheprakov, A. V.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 11; (1988); p. 2029 - 2035; Zhurnal Organicheskoi Khimii; vol. 24; nb. 11; (1988); p. 2251 - 2258 View in Reaxys

Rx-ID: 4032823 View in Reaxys 112/310 Yield 24.2 % Chromat., 12.7 % Chromat.,

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16.0 % Chromat.

C6H4Br2

N O

Rx-ID: 6726728 View in Reaxys 113/310 Yield

Conditions & References With potassium bromide, sodium nitrite in water, trifluoroacetic acid, Time= 0.25h, T= 20 °C , under argon, other reagent, other time, Product distribution Cheprakov, A. V.; Makhon'kov, D. I.; Rodkin, M. A.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 2; (1988); p. 217 - 223; Zhurnal Organicheskoi Khimii; vol. 24; nb. 2; (1988); p. 248 255 View in Reaxys

silver p-toluate

Rx-ID: 6819909 View in Reaxys 114/310 Yield

Conditions & References With iodine Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys Cl Cl

absolute-methanolic hydrochloric acid Cl

Cl Cl

Rx-ID: 7446176 View in Reaxys 115/310 Yield

Conditions & References With graphiteelectrode, Electrolysis, α-benzene hexachloride Jayles; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 189; (1929); p. 686 View in Reaxys

Rx-ID: 8797662 View in Reaxys 116/310 Yield

Conditions & References With oxygen, Formation of xenobiotics, combustion, Further byproducts given. Title compound not separated from byproducts Burfeindt; Homann; Chemosphere; vol. 42; nb. 5-7; (2001); p. 439 - 447 View in Reaxys

S– 2

Zn 2+

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0.5

0.5 Cl

(v2) S–

Zn 2+

(v4)

(v3)

Rx-ID: 27478243 View in Reaxys 117/310 Yield

Conditions & References in chlorobenzene, metal compd. and fullerene (2:1); crystd. on storage for 1 wk, septd., washed (acetone), XRD Konarev, Dmitri V.; Kovalevsky, Andrey Y.; Khasanov, Salavat S.; Saito, Gunzi; Lopatin, Dmitri V.; Umrikhin, Alexey V.; Otsuka, Akihiro; Lyubovskaya, Rimma N.; European Journal of Inorganic Chemistry; nb. 9; (2006); p. 1881 - 1895 ; (from Gmelin) View in Reaxys

Rx-ID: 666186 View in Reaxys 118/310 Yield

Conditions & References T= 75 °C Dannley; Sternfeld; Journal of the American Chemical Society; vol. 76; (1954); p. 4543,4544 View in Reaxys

Rx-ID: 846664 View in Reaxys 119/310 Yield

Conditions & References With aluminium trichloride Anschuetz; Justus Liebigs Annalen der Chemie; vol. 235; (1886); p. 163 View in Reaxys

F F

Rx-ID: 3755906 View in Reaxys 120/310 Yield

Conditions & References

45 %, 40 %, 7 %

With lead(IV) acetate, lithium chloride, Time= 1h, T= 25 °C , other temperature, Mechanism, Product distribution Serguchev, Yu. A.; Davydova, V. G.; Makhon'kov, D. I.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 1006 - 1011; Zhurnal Organicheskoi Khimii; vol. 22; nb. 6; (1986); p. 1121 - 1126 View in Reaxys

Br Br

Rx-ID: 4032775 View in Reaxys 121/310 Yield 19.6 % Chromat.,

Conditions & References Time= 20h, T= 25 °C , Irradiation

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10.5 % Chromat., 8.8 % Chromat., 20.0 % Chromat.

Nakada; Miura; Nishiyama; Higashi; Mori; Hirota; Ishii; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3122 - 3126 View in Reaxys

Cl Cl

Rx-ID: 4812642 View in Reaxys 122/310 Yield

Conditions & References With [Pt(triphenylphosphine)2Cl2] in acetonitrile, T= 110 °C , other reagents, Product distribution, Rate constant Vedernikov; Zazybin; Borisoglebskii; Solomonov; Russian Journal of General Chemistry; vol. 66; nb. 12; (1996); p. 1922 - 1924 View in Reaxys

C–

3 –O

Pb4+

–O

O–

F +B

Pb2+

O (v0)

Rx-ID: 26147950 View in Reaxys 123/310 Yield

Conditions & References

62 %, 6 %

Stirring of Pb-compd. in excess of BF3*Et2O overnight at room temp.; GC anal. Meio, Giuseppe V. De; Pinhey, John T.; Journal of the Chemical Society, Chemical Communications; nb. 15; (1990); p. 1065 - 1066 ; (from Gmelin) View in Reaxys

Rx-ID: 846657 View in Reaxys 124/310 Yield

Conditions & References langsame Neutronen.Irradiation Glueckauf; Fay; Journal of the Chemical Society; (1936); p. 392 View in Reaxys γ-Irradiation, Kinetics Sife-Eldeen; Ebraheem; Journal of the Chinese Chemical Society; vol. 54; nb. 6; (2007); p. 1443 - 1450 View in Reaxys in benzene, other Radiation; radiation with neutrons, formation of radioactive C6H5Cl; Miller, J. M.; Dodson, R. W.; Journal of Chemical Physics; vol. 18; (1950); p. 865 - 875 View in Reaxys vol. C: MVol.D2; 4.1.2.7.4.4, page 227 - 228 ; (from Gmelin) View in Reaxys

F F

Rx-ID: 3918647 View in Reaxys 125/310

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Yield

Conditions & References

33 % Spectr., 27 % Spectr., 7% Spectr., 18 % Spectr., 15 % Spectr.

With tetrafluoroammonium tetrafluoroborate in hydrogen fluoride, T= 0 °C , NF4BF4 to benzene ratio, Product distribution Schack, Carl J.; Christe, Karl O.; Journal of Fluorine Chemistry; vol. 18; (1981); p. 363 - 374 View in Reaxys

O I

Rx-ID: 3918714 View in Reaxys 126/310 Yield

Conditions & References

73 % Chromat., 3 % Chromat.

With sodium nitrate, potassium iodide in water, trifluoroacetic acid, Time= 24h, T= 20 °C , Product distribution Makhon'kov, D. I.; Cheprakov, A. V.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 11; (1988); p. 2029 - 2035; Zhurnal Organicheskoi Khimii; vol. 24; nb. 11; (1988); p. 2251 - 2258 View in Reaxys Cl Cl Cl

Cl Cl

Rx-ID: 3918731 View in Reaxys 127/310 Yield

Conditions & References With chlorine, zeolite REY (SK-500), T= 170 - 180 °C , variation of catalysts, Product distribution Huizinga; Scholten; Wortel; van Bekkum; Tetrahedron Letters; vol. 21; nb. 39; (1980); p. 3809 - 3812 View in Reaxys

Cl Al

O S

1.3-di-sec.-butyl-benzene Rx-ID: 6682802 View in Reaxys 128/310 Yield

Conditions & References T= 0 - 5 °C Barkenbus; Hopkins; Allen; Journal of the American Chemical Society; vol. 61; (1939); p. 2452 View in Reaxys

Cl Cl

pentachloro-cyclohexene

chloro-hydrocarbons

Rx-ID: 6730433 View in Reaxys 129/310 Yield

Conditions & References T= 20 - 30 °C , im Gluehlampen-Licht

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Calingaert et al.; Journal of the American Chemical Society; vol. 73; (1951); p. 5224,5227 View in Reaxys

sulfur dioxide

magnesium Rx-ID: 18176781 View in Reaxys 130/310

Yield

Conditions & References Reaction Steps: 4 1: 19.7 percent Chromat. / 20 h / 25 °C / Irradiation 2: 1.5 percent Chromat. / 20 h / 25 °C / Irradiation 3: 1.3 percent Chromat. / 24 h / 25 °C / Irradiation 4: 19.6 percent Chromat. / 20 h / 25 °C / Irradiation Nakada; Miura; Nishiyama; Higashi; Mori; Hirota; Ishii; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3122 - 3126 View in Reaxys

N (v3)

(v3)

(v2) S–

(v2)

(v3)

S Zn 2+S– SP-5 (v5) S– S

(v5) 2+

Zn S S–SP-5

(v3)

0.5

0.5 Cl

(v2) S–

Zn 2+

N S

(v3)

(v4)

(v3)

Rx-ID: 27478241 View in Reaxys 131/310 Yield

Conditions & References in chlorobenzene, soln. contg. C60 and Zn complex in PhCl evapd. for 1 wk; crystals washed with acetone; dried in air; detd. by X-ray diffraction Konarev; Khasanov; Lopatin; Rodaev; Lyubovskaya; Russian Chemical Bulletin; vol. 56; nb. 11; (2007); p. 2145 - 2161 ; (from Gmelin) View in Reaxys

O O

S I

O O

O HO

Rx-ID: 3918636 View in Reaxys 132/310 Yield

Conditions & References in benzene, Time= 17h, Heating, Yield given Correa, Carlos M. M. da Silva; Oliveira, Maria Augusta B. C. S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 711 - 716 View in Reaxys

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Rx-ID: 3918725 View in Reaxys 133/310 Yield

Conditions & References With chlorine pentafluoride in tetrachloromethane, T= 0 °C , various ClF5 concentration, Product distribution Boudakian, Max M.; Hyde, Gene A.; Journal of Fluorine Chemistry; vol. 25; (1984); p. 435 - 446 View in Reaxys

Cl Cl

Rx-ID: 5247755 View in Reaxys 134/310 Yield

Conditions & References With zeolite NaZSM-5, chlorine, T= 0 °C , Chlorination, Product distribution, Further Variations: Temperatures Kirkby, Scott J.; Frei, Heinz; Journal of Physical Chemistry B; vol. 102; nb. 37; (1998); p. 7106 - 7111 View in Reaxys

Cl Al

Rx-ID: 7061565 View in Reaxys 135/310 Yield

Conditions & References T= 0 - 5 °C Barkenbus; Hopkins; Allen; Journal of the American Chemical Society; vol. 61; (1939); p. 2452 View in Reaxys

Sn Cl

Rx-ID: 8251548 View in Reaxys 136/310 Yield

Conditions & References T= 0 °C Bullard; Robinson; Journal of the American Chemical Society; vol. 49; (1927); p. 1371 View in Reaxys

C6H4Cl2, C12H9Cl Rx-ID: 6726729 View in Reaxys 137/310 Yield

Conditions & References With polychlorobiphenyl, T= 375 °C , effect of reaction time on the product yield/distribution, Product distribution Shinoda, Kiyonori; Yasuda, Kensei; Ohta, Minoru; Chemistry Letters; (1989); p. 1265 - 1266 View in Reaxys

C6H4Cl2 Rx-ID: 6726733 View in Reaxys 138/310

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Yield

Conditions & References With potassium chloride, cobalt acetate tetrahydrate, trifluoroacetic acid, Time= 15h, T= 25 °C , Mn(CH3COO)3, 2 216 h, various conc. of aq. CF3COOH, Product distribution Makhon'kov, D. I.; Cheprakov, A. V.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 22; (1986); p. 609 - 615; Zhurnal Organicheskoi Khimii; vol. 22; nb. 4; (1986); p. 681 - 688 View in Reaxys

O O

O C– N

K+

F O

O F N O

N N

O O

N N

Rx-ID: 3917903 View in Reaxys 139/310 Yield

Conditions & References

22 % Chromat., 5 % Chromat., 1 % Chromat., 14 % Chromat., 1.4 % Chromat.

With XeF2 in acetonitrile, T= 15 - 20 °C , Product distribution, Mechanism Tselinskii, I. V.; Mel'nikov, A. A.; Trubitsin, A. E.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 4; (1988); p. 619 - 622; Zhurnal Organicheskoi Khimii; vol. 24; nb. 4; (1988); p. 688 - 692 View in Reaxys

C6H4Cl2, C6H4(NO2)Cl

N O

Rx-ID: 6726730 View in Reaxys 140/310 Yield

Conditions & References With potassium chloride, potassium nitrate, trifluoroacetic acid, Time= 16.08h, T= 20 °C , other time, other ratio of reagents, other solvent, Product distribution, Mechanism Makhon'kov, D. I.; Cheprakov, A. V.; Rodkin, M. A.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 2; (1988); p. 211 - 217; Zhurnal Organicheskoi Khimii; vol. 24; nb. 2; (1988); p. 241 248 View in Reaxys

O H

H I

racemate

I H

I O

racemate

O H racemate

I Z O

O H

H E

O racemate

O H racemate

Rx-ID: 4209211 View in Reaxys 141/310

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Yield

Conditions & References

55 %, 1 %, With dibenzoyl peroxide, Time= 11h, Heating, study of cyclisation with various types and concentrations of initiators, 2 %, 1 %, solvents, temperatures, reaction time, Product distribution, Mechanism 1 %, 24 % Mawson; Routledge; Weavers; Tetrahedron; vol. 51; nb. 16; (1995); p. 4665 - 4678 View in Reaxys

selenium

Yield

Conditions & References

Rx-ID: 6674800 View in Reaxys 142/310 O'Kelly; Journal of the American Chemical Society; vol. 56; (1934); p. 2783 View in Reaxys

tellane

Rx-ID: 6674801 View in Reaxys 143/310 Yield

Conditions & References O'Kelly; Journal of the American Chemical Society; vol. 56; (1934); p. 2783 View in Reaxys

tellane

iron

Rx-ID: 6674802 View in Reaxys 144/310 Yield

Conditions & References O'Kelly; Journal of the American Chemical Society; vol. 56; (1934); p. 2783 View in Reaxys

F F

nitrogen

F F

O F

Rx-ID: 6676399 View in Reaxys 145/310 Yield

Conditions & References Allison; Cady; Journal of the American Chemical Society; vol. 81; (1959); p. 1089 View in Reaxys

air Rx-ID: 6682771 View in Reaxys 146/310

Yield

Conditions & References T= 180 - 250 °C , Leiten ueber kupferhaltige Mischkatalysatoren Patent; Raschig G.m.b.H.; DE539176; (1930); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 805,807 View in Reaxys Mathes; Angewandte Chemie; vol. 52; (1939); p. 591 View in Reaxys Patent; Raschig G.m.b.H.; US1963761; (1931) View in Reaxys T= 400 °C , Leiten ueber mit Kupferchlorid getraenkten Bimsstein

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Patent; I. G. Farbenind.; DE487596; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 334 View in Reaxys

Rx-ID: 6674793 View in Reaxys 147/310 Yield

Conditions & References Datta; Chatterjee; Journal of the American Chemical Society; vol. 38; (1916); p. 2548 View in Reaxys Cl Cl

iodine trichloride

Cl Cl

Rx-ID: 6682806 View in Reaxys 148/310 Yield

Conditions & References Campaigne; Leal; Journal of the American Chemical Society; vol. 75; (1953); p. 230 View in Reaxys

Rx-ID: 6682922 View in Reaxys 149/310 Yield

Conditions & References Datta; Fernandes; Journal of the American Chemical Society; vol. 36; (1914); p. 1009 View in Reaxys Kempf; Moehrke; Chemische Berichte; vol. 47; (1914); p. 2620; Chem. Zentralbl.; vol. 84; nb. I; (1913); p. 758 View in Reaxys

chloroiodobenzenes

Rx-ID: 6727077 View in Reaxys 150/310 Yield

Conditions & References With iodine, T= 275 °C , Product distribution Mulder, Peter; Louw, Robert; Recueil: Journal of the Royal Netherlands Chemical Society; vol. 103; nb. 10; (1984); p. 282 - 287 View in Reaxys

trinitrophenol Rx-ID: 6731959 View in Reaxys 151/310

Yield

Conditions & References Datta; Chatterjee; Journal of the American Chemical Society; vol. 39; (1917); p. 437 View in Reaxys

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Rx-ID: 666187 View in Reaxys 152/310 Yield

Conditions & References nach Hydrolyse durch Erwaermen mit wss. Natronlauge Dannley; Sternfeld; Journal of the American Chemical Society; vol. 76; (1954); p. 4543,4544 View in Reaxys

Cl Cl

Rx-ID: 3394720 View in Reaxys 153/310 Yield

Conditions & References With PdCl2/C, T= 400 °C , effect of different metal chloride catalyst supported on activated charcoal; effect of other carriers, Mechanism, Product distribution Shinoda, Kiyonori; Chemistry Letters; (1987); p. 2051 - 2052 View in Reaxys O Cl

Rx-ID: 3916999 View in Reaxys 154/310 Yield

Conditions & References

0.03 mol

With tetrachloromethane, Ambient temperature, Irradiation, Product distribution Takahara, Shigeru; Urano, Tishiyuki; Kitamura, Akihide; Sakuragi, Hirochika; Kikuchi, Osamu; et al; Bulletin of the Chemical Society of Japan; vol. 58; nb. 2; (1985); p. 688 - 697 View in Reaxys O

Ag+ Br

O–

Rx-ID: 3918429 View in Reaxys 155/310 Yield 10 %, 16 %

Conditions & References T= 25 °C , Product distribution Bryce-Smith, Derek; Isaacs, Neil S.; Tumi, Seddeg O.; Chemistry Letters; (1984); p. 1471 - 1472 View in Reaxys

Cl Cl

Rx-ID: 5247756 View in Reaxys 156/310 Yield

Conditions & References With chlorine, Chlorination, Product distribution, Further Variations: various wavelengths Kirkby, Scott J.; Frei, Heinz; Journal of Physical Chemistry B; vol. 102; nb. 37; (1998); p. 7106 - 7111 View in Reaxys

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Cl Al

Rx-ID: 6672125 View in Reaxys 157/310 Yield

Conditions & References Sherrill; Journal of the American Chemical Society; vol. 46; (1924); p. 2756 View in Reaxys

iron

Rx-ID: 6682778 View in Reaxys 158/310 Yield

Conditions & References T= 15 - 85 °C Silberman; Sslobodnik; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 10; (1937); p. 1080,1082; Chem. Zentralbl.; vol. 109; nb. II; (1938); p. 1580 View in Reaxys Woroshzow; Silberman; Grigorjew; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 8; (1935); p. 872,875; Chem. Zentralbl.; vol. 107; nb. I; (1936); p. 2825 View in Reaxys Kriwonoss; Ukrainskii Khimicheskii Zhurnal (Russian Edition); vol. 10; (1935); p. 417; Chem. Zentralbl.; vol. 107; nb. I; (1936); p. 4897 View in Reaxys Br Br Br

HBr

Rx-ID: 6728594 View in Reaxys 159/310 Yield

Conditions & References With bromine, Time= 16h, T= 55 °C , Irradiation, temperature, Product distribution Bolton, Roger; Bhangar, Muhammad Iqbal; Williams, Gareth H.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1984); p. 893 - 896 View in Reaxys

Cl O

S Cl

O O

OH O

H 2N 2

sulfur dioxide HO

Rx-ID: 6731495 View in Reaxys 160/310 Yield

Conditions & References Reaktion mit:Produkt5: Biphenyl. Kharasch; Brown; Journal of the American Chemical Society; vol. 61; (1939); p. 2142,2146 View in Reaxys

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Cl Cl

Cl Al

Rx-ID: 7061563 View in Reaxys 161/310 Yield

Conditions & References Fleck; Preston; Haller; Journal of the American Chemical Society; vol. 67; (1945); p. 1419,1420 View in Reaxys

Cl O

Rx-ID: 8606119 View in Reaxys 162/310 Yield

Conditions & References With sodium peroxodisulphate, water, sodium chloride, Irradiation, Substitution, Kinetics Martire; Bertolotti; Braun; Gonzalez; Alegre; Gerones; Rosso; Journal of Physical Chemistry A; vol. 104; nb. 14; (2000); p. 3117 - 3125 View in Reaxys

O P

Cl S

P O

O O

Rx-ID: 730304 View in Reaxys 163/310 Yield

Conditions & References Poshkus; Herweh; Journal of the American Chemical Society; vol. 79; (1957); p. 4245 View in Reaxys

F F

F F F

F F

O F

Rx-ID: 3755901 View in Reaxys 164/310 Yield

Conditions & References With lead(IV) acetate, lithium chloride, Time= 7h, T= 80 °C , various ratio of reagents studied, Product distribution, Mechanism Serguchev, Yu. A.; Davydova, V. G.; Stetsyuk, G. A.; Blendonogii, D. P.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 19; nb. 4; (1983); p. 726 - 730; Zhurnal Organicheskoi Khimii; vol. 19; nb. 4; (1983); p. 820 - 824 View in Reaxys

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Rx-ID: 3917359 View in Reaxys 165/310 Yield

Conditions & References T= 25 °C , ΔH, ΔS, Thermodynamic data Nesterova, T. N.; Rozhnov, A. M.; Malova, T. N.; Kovzel, E. N.; Journal of Chemical Thermodynamics; vol. 17; nb. 7; (1985); p. 649 - 656 View in Reaxys

Cl Cl

Rx-ID: 3918712 View in Reaxys 166/310 Yield

Conditions & References With hydrogenchloride, oxygen, T= 448.9 - 900.9 °C , also benzonitrile, Mechanism, Kinetics Born, Jan G. P.; Wart, Hans W. A. van der; Mulder, Peter; Louw, Robert; Recueil des Travaux Chimiques des Pays-Bas; vol. 112; nb. 4; (1993); p. 262 - 270 View in Reaxys 1

-1

Rx-ID: 4937950 View in Reaxys 167/310 Yield

Conditions & References With bromide, Rate constant Galli, Carlo; Gentili, Patrizia; Acta Chemica Scandinavica; vol. 52; nb. 1; (1998); p. 67 - 76 View in Reaxys

ammonium lead perchloroide PbCl4+2 NH4Cl

Rx-ID: 6682772 View in Reaxys 168/310 Yield

Conditions & References T= 150 °C Seyewetz; Biot; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 135; (1902); p. 1121 View in Reaxys

chlorosulfur Rx-ID: 6682773 View in Reaxys 169/310 Yield

Conditions & References T= 250 °C Schmidt,E.; Chemische Berichte; vol. 11; (1878); p. 1173 View in Reaxys

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disulfur dichloride Rx-ID: 6682776 View in Reaxys 170/310 Yield

Conditions & References T= 250 °C Schmidt,E.; Chemische Berichte; vol. 11; (1878); p. 1173 View in Reaxys

Cl Al

N O

Rx-ID: 7063351 View in Reaxys 171/310 Yield

Conditions & References Produkt: Nitromethan, analog verlaufen die Reaktionen mit Brombenzol, Chlorbenzol und Anisol in Schwefelkohlenstoff Sherrill; Journal of the American Chemical Society; vol. 46; (1924); p. 2756 View in Reaxys

Br N

Rx-ID: 847115 View in Reaxys 172/310 Yield

Conditions & References Merz; Weith; Chemische Berichte; vol. 10; (1877); p. 756 View in Reaxys T= 220 - 240 °C Merz; Weith; Chemische Berichte; vol. 10; (1877); p. 756 View in Reaxys

N Br

H N

N O

N Br

N O

Rx-ID: 3918380 View in Reaxys 173/310 Yield

Conditions & References in benzene, Time= 3h, Heating, other bromo-1-nitro-1H-pyrazoles; var. solvents, temp., time and reagents, Product distribution, Mechanism Juffermans, J. P. H.; Habraken, Clarisse L.; Journal of Organic Chemistry; vol. 51; nb. 24; (1986); p. 4656 - 4660 View in Reaxys

Cl S Cl

Rx-ID: 6682763 View in Reaxys 174/310 Yield

Conditions & References T= 160 °C Dubois; ; (1866); p. 705 View in Reaxys

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Cl Al

SCl2

Rx-ID: 6684490 View in Reaxys 175/310 Yield

Conditions & References T= 60 °C Friedel; Crafts; Annales de Chimie (Cachan, France); vol. <6> 1; (1884); p. 530; Annales de Chimie (Cachan, France); vol. 14; (1888); p. 441 View in Reaxys Krafft; Lyons; Chemische Berichte; vol. 29; (1896); p. 437 View in Reaxys Boeseken; Recueil des Travaux Chimiques des Pays-Bas; vol. 24; (1905); p. 217 View in Reaxys

HBr

Rx-ID: 7076880 View in Reaxys 176/310 Yield

Conditions & References With bromine, Time= 20h, T= 50 °C , Irradiation, other time, reagents ratio, Product distribution Bolton, Roger; Bhangar, Muhammad Iqbal; Williams, Gareth H.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1984); p. 893 - 896 View in Reaxys

Rx-ID: 844396 View in Reaxys 177/310 Yield

Conditions & References T= 500 - 650 °C Schwarz; Pflugmacher; Journal fuer Praktische Chemie (Leipzig); vol. <2> 156; (1940); p. 205,219-223 View in Reaxys

Br Br

Rx-ID: 846737 View in Reaxys 178/310 Yield

Conditions & References T= 500 - 650 °C Schwarz; Pflugmacher; Journal fuer Praktische Chemie (Leipzig); vol. <2> 156; (1940); p. 205,219-223 View in Reaxys

Cl Fe Cl

(v3)

Rx-ID: 6416672 View in Reaxys 179/310

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Yield

Conditions & References T= 100 °C Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys

S OO

Rx-ID: 6585458 View in Reaxys 180/310 Yield

Conditions & References T= 150 °C Neumann; Justus Liebigs Annalen der Chemie; vol. 241; (1887); p. 84 View in Reaxys

Cl Fe Cl

(v3)

Rx-ID: 6585464 View in Reaxys 181/310 Yield

Conditions & References T= 100 °C Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys

Cl Al

Rx-ID: 6682766 View in Reaxys 182/310 Yield

Conditions & References T= 50 - 55 °C Mouneyrat; Pouret; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 127; (1898); p. 1026 View in Reaxys

Cl Cl

Sn ClCl

Rx-ID: 6682769 View in Reaxys 183/310 Yield

Conditions & References T= 30 - 40 °C Patent; Monsanto Chem. Co.; US2111866; (1934) View in Reaxys

chloro trifluoride

cobalt (II)-fluoride

Cl F

Rx-ID: 6682787 View in Reaxys 184/310

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Yield

Conditions & References T= 0 - 77 °C Ellis; Musgrave; Journal of the Chemical Society; (1950); p. 3608 View in Reaxys

chloro trifluoride

metal halides

Cl F

Rx-ID: 6682790 View in Reaxys 185/310 Yield

Conditions & References T= 0 - 77 °C Ellis; Musgrave; Journal of the Chemical Society; (1950); p. 3608 View in Reaxys

Cl Al

Rx-ID: 6682803 View in Reaxys 186/310 Yield

Conditions & References T= 70 - 75 °C Prins; Journal fuer Praktische Chemie (Leipzig); vol. <2>89; (1914); p. 416 View in Reaxys Mouneyrat; Bulletin de la Societe Chimique de France; vol. <3> 19; (1898); p. 555 View in Reaxys O N

N O

N N Br

NH N N O

N O

N N O

NO2, Br2

N O

NH N N O

Rx-ID: 8427402 View in Reaxys 187/310 Yield

Conditions & References

27 %, 7 %, Time= 96h, Heating, Product distribution, Mechanism 23 %, 19 Zibuck, Regina; Stahl, Mark A.; Barchiesi, Bobbi; Waalwijk, Peter S.; Cohen-Fernandes, Pauline; Habraken, %, 1 % Clarisse L.; Journal of Organic Chemistry; vol. 49; nb. 18; (1984); p. 3310 - 3314 View in Reaxys

O O

O N

N N Br

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O Br

NH N

O O

NH N N

NO2, Br2

Rx-ID: 8427403 View in Reaxys 188/310 Yield

Conditions & References

26 %, 10 %, 34 %, 39 %, 1 %

Time= 96h, Heating, Product distribution, Mechanism Zibuck, Regina; Stahl, Mark A.; Barchiesi, Bobbi; Waalwijk, Peter S.; Cohen-Fernandes, Pauline; Habraken, Clarisse L.; Journal of Organic Chemistry; vol. 49; nb. 18; (1984); p. 3310 - 3314 View in Reaxys

Cl Al

OH Cl

Rx-ID: 6416665 View in Reaxys 189/310 Yield

Conditions & References Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

Cl Al

OH Br

Rx-ID: 6416666 View in Reaxys 190/310 Yield

Conditions & References Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

Cl Al

OH Br

Rx-ID: 6416667 View in Reaxys 191/310 Yield

Conditions & References Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

Rx-ID: 6585461 View in Reaxys 192/310 Yield

Conditions & References T= 200 - 240 °C Kekule; Justus Liebigs Annalen der Chemie; vol. 137; (1866); p. 167 View in Reaxys

I Cl

chloro trifluoride

Rx-ID: 6682786 View in Reaxys 193/310

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Yield

Conditions & References T= 0 - 77 °C Ellis; Musgrave; Journal of the Chemical Society; (1950); p. 3608 View in Reaxys

–O

Ag+

Rx-ID: 8259883 View in Reaxys 194/310 Yield

Conditions & References T= 20 °C Birckenbach; Goubeau; Chemische Berichte; vol. 66; (1933); p. 1285,1287 View in Reaxys

F F F

Rx-ID: 847112 View in Reaxys 195/310 Yield

Conditions & References bei der Einwirkung von γ-Strahlen Feng; Mamula; Journal of Chemical Physics; vol. 28; (1958); p. 507 View in Reaxys

I I

Rx-ID: 2856672 View in Reaxys 196/310 Yield

Conditions & References Time= 24h, Irradiation, addition of Et3N, other alkyl iodides, var. solvents, other arenes, Product distribution, Mechanism Kurz, Michael E.; Noreuil, Tim; Seebauer, Joe; Cook, Stephanie; Geier, Douglas; et al.; Journal of Organic Chemistry; vol. 53; nb. 1; (1988); p. 172 - 177 View in Reaxys HO

Cl O

N N

N OH

Rx-ID: 6682770 View in Reaxys 197/310 Yield

Conditions & References T= 38 °C , es erfolgt elektrochemische Chlorierung Ghosh et al.; Journal of Scientific and Industrial Research; vol. 11 B; (1952); p. 356,359 View in Reaxys

Cl Al Cl

Rx-ID: 6682804 View in Reaxys 198/310

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Yield

Conditions & References T= 60 °C Hey; Journal of the Chemical Society; (1935); p. 72,74 View in Reaxys

O Br

asymm.diphenylethane O

Rx-ID: 6726238 View in Reaxys 199/310 Yield

Conditions & References T= 50 °C Anschuetz; Justus Liebigs Annalen der Chemie; vol. 235; (1886); p. 163 View in Reaxys

Cl Al

Br Cl

OH Br

Rx-ID: 7990333 View in Reaxys 200/310 Yield

Conditions & References Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

Cl Al

Br Cl

Br HO

Rx-ID: 7991981 View in Reaxys 201/310 Yield

Conditions & References Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

Cl Al

Br Cl

Br HO

Rx-ID: 8115860 View in Reaxys 202/310 Yield

Conditions & References Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

Rx-ID: 844395 View in Reaxys 203/310 Yield

Conditions & References langsame Neutronen.Irradiation Glueckauf; Fay; Journal of the Chemical Society; (1936); p. 392 View in Reaxys

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Glueckauf; Jacobi; Kitt; Journal of the Chemical Society; (1949); p. Spl. 330, 332 View in Reaxys

F F

Rx-ID: 847111 View in Reaxys 204/310 Yield

Conditions & References Einwirkung von γ-Strahlen Feng; Mamula; Journal of Chemical Physics; vol. 28; (1958); p. 507 View in Reaxys

Rx-ID: 6416668 View in Reaxys 205/310 Yield

Conditions & References Schramm; Chemische Berichte; vol. 18; (1885); p. 607 View in Reaxys Bruner; Chem. Zentralbl.; vol. 71; nb. II; (1900); p. 257 View in Reaxys

Rx-ID: 6585457 View in Reaxys 206/310 Yield

Conditions & References langsame Neutronen.Irradiation Glueckauf; Fay; Journal of the Chemical Society; (1936); p. 392 View in Reaxys Glueckauf; Jacobi; Kitt; Journal of the Chemical Society; (1949); p. Spl. 330, 332 View in Reaxys

O Cl

Rx-ID: 6682764 View in Reaxys 207/310 Yield

Conditions & References im Dunkeln Goldschmidt; Endres; Dirsch; Chemische Berichte; vol. 58; (1925); p. 574 View in Reaxys Klingstedt; Acta Academiae Aboensis, Series B: Mathematica et Physica; vol. 4; nb. 2; p. 22; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 503,504 View in Reaxys

Rx-ID: 6682765 View in Reaxys 208/310 Yield

Conditions & References Patent; Lummus Co.; US2395777; (1942) View in Reaxys

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Patent; Kroeber; DE558068; (1929); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 624 View in Reaxys

O Cl

α-benzene hexachloride

β-benzene hexachloride Rx-ID: 6682784 View in Reaxys 209/310

Yield

Conditions & References im zerstreuten Licht Goldschmidt; Endres; Dirsch; Chemische Berichte; vol. 58; (1925); p. 574 View in Reaxys Klingstedt; Acta Academiae Aboensis, Series B: Mathematica et Physica; vol. 4; nb. 2; p. 22; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 503,504 View in Reaxys

F F

(v3)

O1 N

(v3)

O1N

Rx-ID: 3918420 View in Reaxys 210/310 Yield

Conditions & References Thermodynamic data Stone, John A.; Splinter, Dena E.; Kong, Soon Yau; Canadian Journal of Chemistry; vol. 60; (1982); p. 910 - 915 View in Reaxys

(v3)

O1 N

(v3)

O1N

Rx-ID: 3918422 View in Reaxys 211/310 Yield

Conditions & References Thermodynamic data Stone, John A.; Splinter, Dena E.; Kong, Soon Yau; Canadian Journal of Chemistry; vol. 60; (1982); p. 910 - 915 View in Reaxys O

Rx-ID: 6416664 View in Reaxys 212/310 Yield

Conditions & References Schmidt; Helvetica Chimica Acta; vol. 29; (1946); p. 1144,1147, 1148 View in Reaxys

Ag2SO4 Rx-ID: 6416678 View in Reaxys 213/310

Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284

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AgClO4

Rx-ID: 6416679 View in Reaxys 214/310 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

amalgamated aluminium

Rx-ID: 6416680 View in Reaxys 215/310 Yield

Conditions & References Cohen; Dakin; Journal of the Chemical Society; vol. 75; (1899); p. 894 View in Reaxys

aqueous iron salts

Rx-ID: 6416681 View in Reaxys 216/310 Yield

Conditions & References Menke; ; vol. 31; (1934); p. 344 View in Reaxys

O N

bromosulfur Rx-ID: 6416686 View in Reaxys 217/310

Yield

Conditions & References Edinger; Goldberg; Chemische Berichte; vol. 33; (1900); p. 2884 View in Reaxys

Br H

hypobromous acid Rx-ID: 6416687 View in Reaxys 218/310

Yield

Conditions & References Stark; Chemische Berichte; vol. 43; (1910); p. 672 View in Reaxys

AgClO4

MgO Rx-ID: 6416691 View in Reaxys 219/310

Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

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silver trifluoroacetate

Rx-ID: 6416694 View in Reaxys 220/310 Yield

Conditions & References Haszeldine; Sharpe; Journal of the Chemical Society; (1952); p. 993,1000 View in Reaxys

ZnCl2

Rx-ID: 6416699 View in Reaxys 221/310 Yield

Conditions & References Schiaparelli; Gazzetta Chimica Italiana; vol. 11; (1881); p. 69; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1881); p. 539 View in Reaxys

Cl Al

copper-salt

Rx-ID: 6585469 View in Reaxys 222/310 Yield

Conditions & References Birckenbach; Goubeau; Berninger; Chemische Berichte; vol. 65; (1932); p. 1339,1343 View in Reaxys Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

Cl Al

gold salt

Rx-ID: 6585471 View in Reaxys 223/310 Yield

O N

iodosulfur Rx-ID: 6585472 View in Reaxys 224/310

Yield

Conditions & References Edinger; Goldberg; Chemische Berichte; vol. 33; (1900); p. 2884 View in Reaxys

OH HO

S OO

KIO3 Rx-ID: 6585473 View in Reaxys 225/310

Yield

Conditions & References Peltzer; Justus Liebigs Annalen der Chemie; vol. 136; (1865); p. 201

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View in Reaxys

Cl Al

mercury-salt

Rx-ID: 6585475 View in Reaxys 226/310 Yield

Cl Al

silver-salt

Rx-ID: 6585478 View in Reaxys 227/310 Yield

BeBr2

Rx-ID: 6674795 View in Reaxys 228/310 Yield

Conditions & References Taboury; Pajeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 202; (1936); p. 328 View in Reaxys Pajeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 202; (1936); p. 1795; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 204; (1937); p. 1203 View in Reaxys

CdBr2

Rx-ID: 6674796 View in Reaxys 229/310 Yield

MgBr2

Rx-ID: 6674799 View in Reaxys 230/310 Yield

Conditions & References Taboury; Pajeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 202; (1936); p. 328

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View in Reaxys Pajeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 202; (1936); p. 1795; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 204; (1937); p. 1203 View in Reaxys

ZnBr2

Rx-ID: 6674803 View in Reaxys 231/310 Yield

ZnCl2

Rx-ID: 6674804 View in Reaxys 232/310 Yield

Conditions & References Schmidt; Helvetica Chimica Acta; vol. 29; (1946); p. 1144,1147, 1148 View in Reaxys

Rx-ID: 6682767 View in Reaxys 233/310 Yield

Conditions & References Mueller,H.; Journal of the Chemical Society; vol. 15; (1862); p. 41 View in Reaxys Jungfleisch; Annales de Chimie (Cachan, France); vol. <4> 15; (1868); p. 231,244; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1868); p. 345 View in Reaxys

Cl Fe Cl

(v3)

Rx-ID: 6682768 View in Reaxys 234/310 Yield

Conditions & References Thomas; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 126; (1898); p. 1213; Bulletin de la Societe Chimique de France; vol. <3> 19; (1898); p. 461 View in Reaxys

molybdenum chloride

iron Rx-ID: 6682779 View in Reaxys 235/310

Yield

Conditions & References Lee; ; vol. 54; nb. 11; (1947); p. 118 View in Reaxys

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O Cl

oxygen

H O O

iron oxide

Rx-ID: 6682780 View in Reaxys 236/310 Yield

Conditions & References Licht.Irradiation Patent; Kreidl, Heller and Co.; US1945067; (1930) View in Reaxys Patent; Nozicka; DE526195; (1929); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 520,523 View in Reaxys O Cl

oxygen

iron oxide

Rx-ID: 6682781 View in Reaxys 237/310 Yield

chlorine dioxide Cl O

Rx-ID: 6682801 View in Reaxys 238/310 Yield

Conditions & References Carius; Justus Liebigs Annalen der Chemie; vol. 143; (1867); p. 316 View in Reaxys

Cl Cl

Rx-ID: 6682917 View in Reaxys 239/310 Yield

Conditions & References Mason et al.; Journal of the Chemical Society; (1931); p. 3150,3152, 3154 View in Reaxys Patent; Imp. Chem. Ind.; GB388818; (1931) View in Reaxys 2H

2H 2H

H 2H

HOBr

1.4-dibromo-tetradeuterobenzene 2H

2H 2H

Rx-ID: 7156311 View in Reaxys 240/310 Yield

Conditions & References Best; Wilson; Journal of the Chemical Society; (1946); p. 239,243 View in Reaxys

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Rx-ID: 846741 View in Reaxys 241/310 Yield

Conditions & References Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys F Br

Rx-ID: 4812646 View in Reaxys 242/310 Yield

Conditions & References Time= 24h, Irradiation, Product distribution Song, Yong-Qi; Yuzuri, Tomoaki; Suezawa, Hiroko; Sakakibara, Kazuhisa; Hirota, Minoru; Nakada, Masahiro; Bulletin of the Chemical Society of Japan; vol. 70; nb. 8; (1997); p. 1875 - 1878 View in Reaxys

O O

phenyl magnesium bromide (3 mol)

S Cl

O Cl

Rx-ID: 5930083 View in Reaxys 243/310 Yield

Conditions & References Burton; Davy; Journal of the Chemical Society; (1948); p. 528 View in Reaxys Le Fevre; Markham; Journal of the Chemical Society; (1934); p. 703 View in Reaxys Br

Cl Al

Rx-ID: 6208351 View in Reaxys 244/310 Yield

Conditions & References Kohn; Mueller; Monatshefte fuer Chemie; vol. 30; (1909); p. 407 View in Reaxys

Cl Al

Rx-ID: 6416669 View in Reaxys 245/310 Yield

Conditions & References Leroy; Bulletin de la Societe Chimique de France; vol. <2> 48; (1887); p. 211 View in Reaxys

Rx-ID: 6416670 View in Reaxys 246/310

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Yield

Conditions & References Schramm; Chemische Berichte; vol. 18; (1885); p. 607 View in Reaxys

–O

Ag+

Rx-ID: 6416671 View in Reaxys 247/310 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

Ag+

O–

N O

Rx-ID: 6416673 View in Reaxys 248/310 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

-2 (v1)

(v1)

Cu 2+ S O O

Rx-ID: 6416675 View in Reaxys 249/310 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

(v1)

-2

Hg 2+ O

(v1)

S OO

Rx-ID: 6416676 View in Reaxys 250/310 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

Cl Al

Rx-ID: 6585459 View in Reaxys 251/310 Yield

Conditions & References Greene; Bulletin de la Societe Chimique de France; vol. <2> 36; (1881); p. 234 View in Reaxys

I Cl

(v3)

Rx-ID: 6585460 View in Reaxys 252/310

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Yield

Conditions & References Meyer,L.; Justus Liebigs Annalen der Chemie; vol. 231; (1885); p. 195; Journal fuer Praktische Chemie (Leipzig); vol. <2> 34; (1886); p. 504 View in Reaxys

vanadium

Rx-ID: 6672368 View in Reaxys 253/310 Yield

Conditions & References Schwarz; Pflugmacher; Journal fuer Praktische Chemie (Leipzig); vol. <2> 156; (1940); p. 205,219-223 View in Reaxys

O N

silver-<4-nitro benzoate>

Rx-ID: 6674424 View in Reaxys 254/310 Yield

Conditions & References Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys

Rx-ID: 6674792 View in Reaxys 255/310 Yield

Conditions & References Couper; Annales de Chimie (Cachan, France); vol. <3> 52; (1858); p. 309; Justus Liebigs Annalen der Chemie; vol. 104; (1857); p. 225 View in Reaxys O

Fe Cl

(v3)

Rx-ID: 6674794 View in Reaxys 256/310 Yield

Conditions & References Schmidt; Helvetica Chimica Acta; vol. 29; (1946); p. 1144,1147, 1148 View in Reaxys

charcoal

Yield

Conditions & References

Rx-ID: 6674797 View in Reaxys 257/310 Nikolajew; Zhurnal Obshchei Khimii; vol. 1; (1931); p. 1035; Chem. Zentralbl.; vol. 104; nb. I; (1933); p. 1428 View in Reaxys

manganese

Rx-ID: 6674798 View in Reaxys 258/310 Yield

Conditions & References Gay; Ducelliez; Raynaud; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p. 1804; Bulletin de la Societe Chimique de France; vol. <4> 15; (1914); p. 737

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View in Reaxys

Cl Al

CS2

Rx-ID: 6682775 View in Reaxys 259/310 Yield

Conditions & References Olivier; Recueil des Travaux Chimiques des Pays-Bas; vol. 33; (1914); p. 130,152; Chem. Zentralbl.; vol. 85; nb. I; (1914); p. 2166 View in Reaxys

AlCl3

N+

Rx-ID: 6682794 View in Reaxys 260/310 Yield

Conditions & References beim Behandeln von Benzoldiazoniumchlorid Moehlau; Berger; Chemische Berichte; vol. 26; (1893); p. 2001; Chemische Berichte; vol. 30; (1897); p. 370 Anm. View in Reaxys

Cl S Cl

Rx-ID: 6682797 View in Reaxys 261/310 Yield

Conditions & References Silberrad; Journal of the Chemical Society; vol. 119; (1921); p. 2031 View in Reaxys

iron

Rx-ID: 6682798 View in Reaxys 262/310 Yield

Conditions & References Kinetics Bourion; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 1319; Annales de Chimie (Cachan, France); vol. <9> 14; (1920); p. 297 View in Reaxys

N N

N H

Rx-ID: 6682809 View in Reaxys 263/310 Yield

Conditions & References Patent; Cassella; DE870106; (1938) View in Reaxys Patent; Gen. Aniline and Film Corp.; US2280504; (1939) View in Reaxys Elks; Hey; Journal of the Chemical Society; (1943); p. 441,443 View in Reaxys

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Cl Al

Rx-ID: 6682918 View in Reaxys 264/310 Yield

Conditions & References Mason et al.; Journal of the Chemical Society; (1931); p. 3150,3152, 3154 View in Reaxys Patent; Imp. Chem. Ind.; GB388818; (1931) View in Reaxys

Cl Cl

Rx-ID: 6682919 View in Reaxys 265/310 Yield

Conditions & References Mason et al.; Journal of the Chemical Society; (1931); p. 3150,3152, 3154 View in Reaxys Patent; Imp. Chem. Ind.; GB388818; (1931) View in Reaxys

Cl Cl

(v3)

Rx-ID: 6682920 View in Reaxys 266/310 Yield

Conditions & References Mason et al.; Journal of the Chemical Society; (1931); p. 3150,3152, 3154 View in Reaxys Patent; Imp. Chem. Ind.; GB388818; (1931) View in Reaxys

aluminium

Rx-ID: 6682921 View in Reaxys 267/310 Yield

Conditions & References Meunier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 1451; Bulletin de la Societe Chimique de France; vol. <4> 27; (1920); p. 696 View in Reaxys

Cl Al Cl

Br Br

Rx-ID: 6712568 View in Reaxys 268/310 Yield

Conditions & References Kohn; Mueller; Monatshefte fuer Chemie; vol. 30; (1909); p. 407 View in Reaxys

m-toluic acid phenyl ester

Rx-ID: 6729615 View in Reaxys 269/310 Yield

Conditions & References Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724

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View in Reaxys Br

Cl Al

Rx-ID: 7048468 View in Reaxys 270/310 Yield

Conditions & References Kohn; Fink; Monatshefte fuer Chemie; vol. 44; (1923); p. 187 View in Reaxys

Cl Al

Rx-ID: 7067184 View in Reaxys 271/310 Yield

Conditions & References Kohn; Monatshefte fuer Chemie; vol. 58; (1931); p. 108,110 View in Reaxys O Br

Cl Al

Rx-ID: 7449806 View in Reaxys 272/310 Yield

Conditions & References Kohn; Fink; Monatshefte fuer Chemie; vol. 44; (1923); p. 185,190 View in Reaxys Cl Br

Cl Al

Cl Br

Rx-ID: 8115290 View in Reaxys 273/310 Yield

Conditions & References Kohn; Zandmann; Monatshefte fuer Chemie; vol. 47; (1926); p. 376 View in Reaxys

Rx-ID: 846662 View in Reaxys 274/310 Yield

Conditions & References Anschuetz; Justus Liebigs Annalen der Chemie; vol. 235; (1886); p. 163 View in Reaxys

Br Br

Rx-ID: 847501 View in Reaxys 275/310

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Yield

Conditions & References Anschuetz; Justus Liebigs Annalen der Chemie; vol. 235; (1886); p. 163 View in Reaxys

H 2N

Rx-ID: 5802430 View in Reaxys 276/310 Yield

Conditions & References Seide; Scherlin; Bras; Journal fuer Praktische Chemie (Leipzig); vol. <2>138; (1933); p. 225,228 View in Reaxys

S O

H 2N 2

Rx-ID: 5914109 View in Reaxys 277/310 Yield

Conditions & References reagiert das Silber-Salz Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys

Rx-ID: 5930079 View in Reaxys 278/310 Yield

Conditions & References Elks; Hey; Journal of the Chemical Society; (1943); p. 441,443 View in Reaxys

OH S OO

Rx-ID: 6585465 View in Reaxys 279/310 Yield

Conditions & References Varma; Sreenivasmurthyachar; Journal of the Indian Chemical Society; vol. 13; (1936); p. 187 View in Reaxys

O N

Rx-ID: 6674423 View in Reaxys 280/310 Yield

Conditions & References Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys

Cl Fe Cl

(v3)

Rx-ID: 6674709 View in Reaxys 281/310 Yield

Conditions & References Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys

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Br O

NaBr Br

Rx-ID: 6674775 View in Reaxys 282/310 Yield

Conditions & References es erfolgt elektrochemische Bromierung Bionda; Civera; Annali di Chimica (Rome, Italy); vol. 41; (1951); p. 814,817 View in Reaxys O

N HO

S OO

Rx-ID: 6674805 View in Reaxys 283/310 Yield

Conditions & References Schmidt; Helvetica Chimica Acta; vol. 29; (1946); p. 1144,1147, 1148 View in Reaxys

S OO

Hg2SO4

Rx-ID: 6674816 View in Reaxys 284/310 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 67; (1934); p. 917,920, 926 View in Reaxys

S OO

KIO3

Rx-ID: 6674817 View in Reaxys 285/310 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 67; (1934); p. 917,920, 926 View in Reaxys

sodium persulfate

Rx-ID: 6674818 View in Reaxys 286/310 Yield

Conditions & References Elbs; Jaroslawzew; Journal fuer Praktische Chemie (Leipzig); vol. <2> 88; (1913); p. 92 View in Reaxys

Cl Al

α.β-dibromo-α-phenyl-ethane

Rx-ID: 6681979 View in Reaxys 287/310 Yield

Conditions & References Schramm; Chemische Berichte; vol. 26; (1893); p. 1706 View in Reaxys

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I O

OH H 2N 2

I O

Rx-ID: 6682197 View in Reaxys 288/310 Yield

Conditions & References Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys

Cl Al

N+

Cl –

Rx-ID: 6682793 View in Reaxys 289/310 Yield

Conditions & References Moehlau; Berger; Chemische Berichte; vol. 26; (1893); p. 2001; Chemische Berichte; vol. 30; (1897); p. 370 Anm. View in Reaxys

Cl Al

S Cl

O S

Rx-ID: 6683458 View in Reaxys 290/310 Yield

Conditions & References Boeeseken; Recueil des Travaux Chimiques des Pays-Bas; vol. 30; (1911); p. 385 View in Reaxys

hexachlorocyclohexane

Cl Cl

Rx-ID: 6728660 View in Reaxys 291/310 Yield

Conditions & References Electrolysis Jeunehomme; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 199; (1934); p. 1027; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 32; (1935); p. 173,176 View in Reaxys

O E

I O

meso-1.2-dibenzoyloxy-1.2-diphenyl-ethane Rx-ID: 7080612 View in Reaxys 292/310

Yield

Conditions & References Perret; Perrot; Helvetica Chimica Acta; vol. 28; (1945); p. 558,574 View in Reaxys

O O

H 2N 2

Rx-ID: 7445528 View in Reaxys 293/310

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Yield

Conditions & References Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys

I Hg

(v2)

mercury iodide Rx-ID: 8279872 View in Reaxys 294/310

Yield

Conditions & References bei laengerem Kochen Hilpert; Gruettner; Chemische Berichte; vol. 47; (1914); p. 184 View in Reaxys

Ag+ O

F F

F O

O–

F F

Rx-ID: 8540211 View in Reaxys 295/310 Yield

Conditions & References Swarts; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 27; (1929); p. 683; Chem. Zentralbl.; vol. 101; nb. I; (1930); p. 1763 View in Reaxys

Rx-ID: 846663 View in Reaxys 296/310 Yield

Conditions & References Anschuetz; Justus Liebigs Annalen der Chemie; vol. 235; (1886); p. 163 View in Reaxys

Rx-ID: 5806754 View in Reaxys 297/310 Yield

Conditions & References beim Erwaermen von Silberbenzoat Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys

(v2)

tri-α-naphthyl bismuth dibromide

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(v2)

Br Hg

(v2)

Rx-ID: 5818292 View in Reaxys 298/310 Yield

Conditions & References weitere Produkte:Triphenylwismut,Diphenyl-α-naphthyl-wismut, α-Brom-naphthalin Challenger; Allpress; Journal of the Chemical Society; vol. 119; (1921); p. 916 View in Reaxys

Cl Fe Cl

(v3)

Rx-ID: 5855906 View in Reaxys 299/310 Yield

Conditions & References Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys

Cl Al

Rx-ID: 5856162 View in Reaxys 300/310 Yield

Conditions & References Schramm; Chemische Berichte; vol. 26; (1893); p. 1706 View in Reaxys

O O

O N

HO O

OH O

H 2N 2

Rx-ID: 5914125 View in Reaxys 301/310 Yield

Conditions & References Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys

Cl Al

Rx-ID: 5930084 View in Reaxys 302/310 Yield

Conditions & References Olivier; Recueil des Travaux Chimiques des Pays-Bas; vol. 33; (1914); p. 130,152; Chem. Zentralbl.; vol. 85; nb. I; (1914); p. 2166 View in Reaxys

Br O

Ag+

O–

Rx-ID: 6416674 View in Reaxys 303/310

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Yield

Conditions & References Derbyshire; Waters; Journal of the Chemical Society; (1950); p. 573,576 View in Reaxys

(v1)

OH HO

S OO

-2

2 Ag+ (v1)

S OO

Rx-ID: 6585463 View in Reaxys 304/310 Yield

Conditions & References Barker; Waters; Journal of the Chemical Society; (1952); p. 150,152 View in Reaxys

Fe Cl

(v3)

Rx-ID: 6674183 View in Reaxys 305/310 Yield

Conditions & References Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys

(v1)

OH HO

S OO

-2

(v1)

Hg 2+ O

S OO

Rx-ID: 6674815 View in Reaxys 306/310 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 67; (1934); p. 917,920, 926 View in Reaxys

diselenium dibromide

Se Se

Rx-ID: 6676513 View in Reaxys 307/310 Yield

Conditions & References Loevenich; Sipmann; Journal fuer Praktische Chemie (Leipzig); vol. <2> 124; (1929); p. 132 View in Reaxys

N Br

Cl Al

Rx-ID: 6681861 View in Reaxys 308/310 Yield

Conditions & References Scholl; Noerr; Chemische Berichte; vol. 33; (1900); p. 1056 View in Reaxys

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O S

Cl Al

O O

S O

S Cl

Rx-ID: 6682980 View in Reaxys 309/310 Yield

Conditions & References Toehl; Eberhard; Chemische Berichte; vol. 26; (1893); p. 2942 View in Reaxys

(v2)

Br Hg

(v2)

Rx-ID: 762270 View in Reaxys 310/310 Yield

Conditions & References weitere Produkten: Triphenylwismut, Diphenyl-α-naphthyl-wismut, 1-Brom-naphthalin Challenger; Allpress; Journal of the Chemical Society; vol. 119; (1921); p. 916 View in Reaxys

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