2-Fluorobenzonitrile by Asch

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Reactions (41)

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Citations (60)

References

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Rx-ID: 1767977 Find similar reactions

With potassium fluoride in various solvent(s) T=290°C; P=2206.5 Torr; 2 h;

Suzuki, Hiroshi; Kimura, Yoshikazu

Journal of Fluorine Chemistry, 1991 , vol. 52, # 3 p. 341 - 351 Title/Abstract Full Text View citing articles Show Details

With tetrabutyl ammonium fluoride in dimethyl sulfoxide

T=20°C; 18 h;

Sun, Haoran; DiMagno, Stephen G.

Angewandte Chemie - International Edition, 2006 , vol. 45, # 17 p. 2720 - 2725 Title/Abstract Full Text View citing articles Show Details

95.8 %Chromat.

With tetrabutyl ammonium fluoride in tetrahydrofuran

T=20°C; 30 h; Inert atmosphere; chemoselective reaction;

Hu, Yu Feng; Luo, Jun; Lue, Chun Xu

Chinese Chemical Letters, 2010 , vol. 21, # 2 p. 151 - 154 Title/Abstract Full Text View citing articles Show Details

28 %Spectr.

With p-methoxybenzoyl fluoride; 1,3-diisopropyl-4,5dimethylimidazol-2-ylidene in N,N-dimethyl-formamide

T=25°C; 16 h; Inert atmosphere;

Ryan, Sarah J.; Schimler, Sydonie D.; Bland, Douglas C.; Sanford, Melanie S.

Organic Letters, 2015 , vol. 17, # 8 p. 1866 - 1869 Title/Abstract Full Text View citing articles Show Details

76%

100 %Spectr.

With tetramethylammonium fluoride in N,N-dimethyl-formamide

T=80°C; 24 h; Sealed tube; Reagent/catalystTemperatureTime;

Schimler, Sydonie D.; Ryan, Sarah J.; Bland, Douglas C.; Anderson, John E.; Sanford, Melanie S.

Journal of Organic Chemistry, 2015 , vol. 80, # 24 p. 12137 - 12145 Title/Abstract Full Text View citing articles Show Details

94 %Spectr.

With tetramethylammonium fluoride in N,N-dimethyl-formamide

T=80°C; 3 h; TemperatureReagent/catalyst; Hide Experimental Procedure

DOW AGROSCIENCES LLC; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; SANFORD, Melanie; RYAN, Sarah; SCHIMLER, Sydonie; CHENG, Yang; BLAND, Douglas

Patent: WO2017/24167 A1, 2017 ; Location in patent: Page/Page column 22-23; 36 ; Title/Abstract Full Text Show Details

The reactions of 3a-e with anhydrous NMe F were compared to those with CsF, a more traditional reagent for SNAT fluorination. At 80 °C, CsF afforded <5percent yield of 4 in all cases. At 140 °C (more typical conditions for CsF halex reactions) (JP 2011 153115 A: WO 2010018857; WO 2009014100: Hyohdoh, I.; et al., ACS Med. Chem. Lett. 2013;4: 1059: Finger, G.C.; et al, J. Am. Chem. Soc. 1956;78:6034), the aryl halides 3a-c reacted with CsF to afford 4 in moderate 22-52percent yield (entries 1-3). In all of these cases, unreacted starting material remained after 24 h at 140 °C.

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Rx-ID: 3569591 Find similar reactions

95%

With tetrabutyl ammonium fluoride in tetrahydrofuran

0.166667 h; Inert atmosphereMicrowave irradiation;

LaBeaume, Paul; Placzek, Michael; Daniels, Mathew; Kendrick, Ian; Ng, Patrick; McNeel, Melissa; Afroze, Roushan; Alexander, Abigail; Thomas, Rhiannon; Kallmerten, Amy E.; Jones, Graham B.

Tetrahedron Letters, 2010 , vol. 51, # 14 p. 1906 - 1909 Title/Abstract Full Text View citing articles Show Details

100 % Chromat.

With tetramethylammonium fluoride in dimethyl sulfoxide

T=80°C; 1 h;

Boechat, Nubia; Clark, James H.

Journal of the Chemical Society, Chemical Communications, 1993 , # 11 p. 921 - 922 Title/Abstract Full Text View citing articles Show Details

With tetrabutyl ammonium fluoride in dimethyl sulfoxide

T=20°C; 0.166667 h;

Sun, Haoran; DiMagno, Stephen G.

Angewandte Chemie - International Edition, 2006 , vol. 45, # 17 p. 2720 - 2725 Title/Abstract Full Text View citing articles Show Details

97.3 %Chromat.

With tetrabutyl ammonium fluoride in tetrahydrofuran

T=20°C; 1 h; Inert atmosphere; chemoselective reaction;

Hu, Yu Feng; Luo, Jun; Lue, Chun Xu

Chinese Chemical Letters, 2010 , vol. 21, # 2 p. 151 - 154 Title/Abstract Full Text View citing articles Show Details

99 %Spectr.

With p-methoxybenzoyl fluoride; 1,3-diisopropyl-4,5dimethylimidazol-2-ylidene in N,N-dimethyl-formamide

T=25°C; 16 h; Inert atmosphere;

Ryan, Sarah J.; Schimler, Sydonie D.; Bland, Douglas C.; Sanford, Melanie S.

Organic Letters, 2015 , vol. 17, # 8 p. 1866 - 1869 Title/Abstract Full Text View citing articles Show Details

97 %Spectr.

With tetramethylammonium fluoride in N,N-dimethyl-formamide

T=80°C; 3 h; Sealed tube; Reagent/catalystTemperature;

Schimler, Sydonie D.; Ryan, Sarah J.; Bland, Douglas C.; Anderson, John E.; Sanford, Melanie S.

Journal of Organic Chemistry, 2015 , vol. 80, # 24 p. 12137 - 12145 Title/Abstract Full Text View citing articles Show Details

97 %Spectr.

With tetramethylammonium fluoride in N,N-dimethyl-formamide

T=80°C; 3 h; TemperatureReagent/catalyst; Hide Experimental Procedure

DOW AGROSCIENCES LLC; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; SANFORD, Melanie; RYAN, Sarah; SCHIMLER, Sydonie; CHENG, Yang; BLAND, Douglas

Patent: WO2017/24167 A1, 2017 ; Location in patent: Page/Page column 22-23; 36 ; Title/Abstract Full Text Show Details

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Rx-ID: 28592811 Find similar reactions

80%

With formic acid; hydroxylamine hydrochloride

20 h; Reflux;

Xi, Guoqin; Han, Xiuling; Lu, Xiyan

Advanced Synthesis and Catalysis, 2012 , vol. 354, # 14-15 p. 2701 - 2705,5 Title/Abstract Full Text Show Details

77%

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium perchlorate; acetic acid; lithium hexamethyldisilazane in acetonitrile

Chen, Qiguo; Fang, Chaojie; Shen, Zhenlu; Li, Meichao

Electrochemistry Communications, 2016 , vol. 64, p. 51 - 55 Title/Abstract Full Text View citing articles Show Details

12 h; Electrochemical reaction; Hide Experimental Procedure

General procedure: Preparative electrolysis experiments were performed using 263 APotentiostat/Galvanostat (Princeton Applied Research, USA). 0.1 MNaClO4–CH3CN solution (10 mL) containing aldehydes (1 mmol),TEMPO (0.1 mmol), HMDS (2.5mmol) and AcOH (2.5mmol) was electrolyzedwith stirring in an undivided cell (30 mL) equipped with twoplatinum sheets as anode (1.5 cm2) and cathode (3.0 cm2) respectivelyat a constant potential of 1.5 V vs Ag/Ag+ (0.1MAgNO3 in acetonitrile).The electrode separation was 1 cm. When the reaction was finished,10mL of saturatedNa2SO3 solution was added into the reactionmixtureand stirred for 15 min. Then the mixture was extracted with CH2Cl2(20 mL × 3). The organic layer was dried with anhydrous Na2SO4 andconcentrated in a rotary evaporator. The productswere obtained via purificationof column chromatography and their structures were confirmedby 1H NMR, 13C NMR and MS. NMR was performed on a BrukerAvance III spectrometer. GC-MS was performed on the Thermo TraceISQ instrument with TG 5MS capillary column. 68%

7 %Chromat.

With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; ammonium acetate; sodium perchlorate in acetonitrile

T=20°C; Electrolysis; Reagent/catalyst;

Yang, Xianjing; Fan, Zhongquan; Shen, Zhenlu; Li, Meichao

Electrochimica Acta, 2017 , vol. 226, p. 53 - 59 Title/Abstract Full Text View citing articles Show Details

With tert.-butylhydroperoxide; ammonia; potassium iodide in water

T=60°C; 8 h;

Rajender Reddy; Uma Maheswari; Venkateshwar; Prashanthi; Lakshmi Kantam

Tetrahedron Letters, 2009 , vol. 50, # 18 p. 2050 - 2053 Title/Abstract Full Text View citing articles Show Details

With hydroxylamine hydrochloride; zinc trifluoromethanesulfonate in toluene

T=100°C; 24 h; Hide Experimental Procedure

Enthaler, Stephan; Weidauer, Maik; Schroeder, Fanny

Tetrahedron Letters, 2012 , vol. 53, # 7 p. 882 - 885 Title/Abstract Full Text View citing articles Show Details

General procedure for the synthesis of nitriles: A pressure tube was charged with an appropriate amount of Zn(OTf)2 (0.036 mmol, 5.0 mol percent), the corresponding aldehyde (0.72 mmol) and hydroxylamine hydrochloride (1.2 equiv, 0.86 mmol). After the addition of toluene (2.0 mL) the reaction mixture was stirred in a preheated oil bath at 100 °C for 24 h. The mixture was cooled in an ice bath and biphenyl (internal standard) was added. The solution was diluted with dichloromethane and an aliquot was taken for GC-analysis (30 m Rxi-5 ms column, 40-300 °C). The solvent was carefully removed and the residue was purified by column chromatography (n-hexane/ethyl acetate). The analytical properties of the corresponding nitriles are in agreement with the literature. 100 %Spectr.

With [BMIM(SO3H)][OTf]; trimethylsilylazide; 3-butyl-1-methyl-1Himidazol-3-ium hexafluorophosphate

T=20 - 50°C; Schmidt Reaction; 3 h; Sonication;

Nandi, Ganesh C.; Laali, Kenneth K.

Tetrahedron Letters, 2013 , vol. 54, # 17 p. 2177 - 2179 Title/Abstract Full Text View citing articles Show Details

With formic acid; hydroxylamine hydrochloride; sodium acetate in water

T=80°C; Hide Experimental Procedure

Lin, Hong-Yan; Li, Zi-Kang; Bai, Li-Fei; Baloch, Shahla Karim; Wang, Fang; Qiu, Han-Yue; Wang, Xue; Qi, Jin-Liang; Yang, Raong-Wu; Wang, Xiao-Ming; Yang, Yong-Hua

Biochemical Pharmacology, 2015 , vol. 96, # 2 p. 93 - 106 Title/Abstract Full Text View citing articles Show Details

General procedure for preparation of compounds a1–a17

General procedure: A mixture of aromatic aldehydes (50mmol) (1–17), hydroxylamine hydrochloride (62.5mmol), sodium acetate (125mmol) were dissolved in the mixture of formic acid and water (60:40) and stirred at 80°C until TLC analysis indicated the disappearance of aromatic aldehydes. Then, cooling the reaction system to room temperature and put it into water to obtain the target compounds. Some desired products which were dissolved in the mixture of water and formic acid can be obtained by salting out. Then, solid target compounds were obtained by filtration and recrystallized by alcohol, and then dried under vacuum. While, some target compounds are oily. These oily compounds were obtained by extraction with ethyl acetate and the solvent was removed at the vacuum to afford aryl nitriles (a1–a17).

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Rx-ID: 41657022 Find similar reactions

95 %Spectr.

With tetramethylammonium fluoride in N,N-dimethyl-formamide

T=80°C; 3 h; Sealed tube; Reagent/catalystTemperature;

Schimler, Sydonie D.; Ryan, Sarah J.; Bland, Douglas C.; Anderson, John E.; Sanford, Melanie S.

Journal of Organic Chemistry, 2015 , vol. 80, # 24 p. 12137 - 12145 Title/Abstract Full Text View citing articles Show Details

95 %Spectr.

With tetramethylammonium fluoride in N,N-dimethyl-formamide

T=80°C; 3 h; TemperatureReagent/catalyst; Hide Experimental Procedure

DOW AGROSCIENCES LLC; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; SANFORD, Melanie; RYAN, Sarah; SCHIMLER, Sydonie; CHENG, Yang; BLAND, Douglas

Patent: WO2017/24167 A1, 2017 ; Location in patent: Page/Page column 22-23; 36 ; Title/Abstract Full Text Show Details

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Rx-ID: 41657023 Find similar reactions

88 %Spectr.

With tetramethylammonium fluoride in N,N-dimethyl-formamide

T=80°C; 3 h; Sealed tube; Reagent/catalystTemperature;

Schimler, Sydonie D.; Ryan, Sarah J.; Bland, Douglas C.; Anderson, John E.; Sanford, Melanie S.

Journal of Organic Chemistry, 2015 , vol. 80, # 24 p. 12137 - 12145 Title/Abstract Full Text View citing articles Show Details

88 %Spectr.

With tetramethylammonium fluoride in N,N-dimethyl-formamide

T=80°C; 3 h; TemperatureReagent/catalyst; Hide Experimental Procedure

DOW AGROSCIENCES LLC; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; SANFORD, Melanie; RYAN, Sarah; SCHIMLER, Sydonie; CHENG, Yang; BLAND, Douglas

Patent: WO2017/24167 A1, 2017 ; Location in patent: Page/Page column 22-23; 36 ; Title/Abstract Full Text Show Details

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Rx-ID: 41657024 Find similar reactions

73 %Spectr.

With cesium fluoride in N,N-dimethyl-formamide

T=140°C; 24 h; Sealed tube; Reagent/catalystTemperature;

Schimler, Sydonie D.; Ryan, Sarah J.; Bland, Douglas C.; Anderson, John E.; Sanford, Melanie S.

Journal of Organic Chemistry, 2015 , vol. 80, # 24 p. 12137 - 12145 Title/Abstract Full Text View citing articles Show Details

73 %Spectr.

With cesium fluoride in N,N-dimethyl-formamide

T=140°C; 24 h; TemperatureReagent/catalyst; Hide Experimental Procedure

DOW AGROSCIENCES LLC; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; SANFORD, Melanie; RYAN, Sarah; SCHIMLER, Sydonie; CHENG, Yang; BLAND, Douglas

Patent: WO2017/24167 A1, 2017 ; Location in patent: Page/Page column 22-23; 36 ; Title/Abstract Full Text Show Details

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With ammonia; oxygen in tert-Amyl alcohol; water

T=130°C; P=3750.38 Torr; 24 h;

Rx-ID: 44460998 Find similar reactions

Mao, Fei; Qi, Zhengliang; Fan, Haipeng; Sui, Dejun; Chen, Rizhi; Huang, Jun

RSC Advances, 2017 , vol. 7, # 3 p. 1498 - 1503 Title/Abstract Full Text View citing articles Show Details

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With 5 active carbon-supported ruthenium; oxygen in toluene

Rx-ID: 44752133 Find similar reactions

Niu, Baoqiang; Lu, Fei; Zhang, Hong-Yu; Zhang, Yuecheng; Zhao, Jiquan

T=150°C; P=3750.38 Torr; 4 h; Autoclave; Hide Experimental Procedure

Chemistry Letters, 2017 , vol. 46, # 3 p. 330 - 333 Title/Abstract Full Text View citing articles Show Details

General procedure: In a typical process, into a 25 ml autoclave equipped with a magnetic stirrer were added 5percentRu/AC (0.03 mmol, 3 molpercent), benzylamine (1 mmol), 5 mL toluene at room temperature successively. After which the resulting reaction mixture was heated at 150 °C for 4 h under 0.5 MPa of oxygen atmosphere. The final reaction conversion and selectivity towards the corresponding nitriles were determined by Gas Chromatograph. After reaction, the product was purified by column chromatography of the reaction mixture on neutral alumina using hexanes/dichloromethane (80:20) or hexanes/EtOAc (30:1) as eluent.

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With tetramethylammonium fluoride in N,N-dimethyl-formamide

T=80°C; 24 h; Inert atmosphereGloveboxSealed tube;

Rx-ID: 44761697 Find similar reactions

Schimler, Sydonie D.; Cismesia, Megan A.; Hanley, Patrick S.; Froese, Robert D.J.; Jansma, Matthew J.; Bland, Douglas C.; Sanford, Melanie S.

Journal of the American Chemical Society, 2017 , vol. 139, # 4 p. 1452 - 1455 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: sulphuryl fluoride; potassium carbonate / ethyl acetate / 4 h / 20 °C 2: tetramethylammonium fluoride / N,N-dimethyl-formamide / 24 h / 80 °C / |Inert atmosphere; |Glovebox; |Sealed tube View Scheme

Rx-ID: 44761709 Find similar reactions

Schimler, Sydonie D.; Cismesia, Megan A.; Hanley, Patrick S.; Froese, Robert D.J.; Jansma, Matthew J.; Bland, Douglas C.; Sanford, Melanie S.

Journal of the American Chemical Society, 2017 , vol. 139, # 4 p. 1452 - 1455 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 45539217 Find similar reactions

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70%

With palladium diacetate; cyclohexyldiphenylphosphine in 1,4dioxane

T=150°C; 16 h; Inert atmosphereSchlenk technique; chemoselective reaction;

Shi, Shicheng; Szostak, Michal

Organic Letters, 2017 , vol. 19, # 12 p. 3095 - 3098 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 45552942 Find similar reactions

A: 65%

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N,Ndimethylethylenediamine; copper(l) chloride in toluene

T=80°C; 24 h; Sealed tubeSchlenk technique; chemoselective reaction; Hide Experimental Procedure

Ma, Xian-Tao; Xu, Hao; Xiao, Ying-Lin; Su, Chen-Liang; Liu, Jian-Ping; Xu, Qing

Chinese Chemical Letters, 2017 , vol. 28, # 6 p. 1336 - 1339 Title/Abstract Full Text View citing articles Show Details

Typical procedures for Cu-catalyzed aerobic oxidation of primary amines with air for nitrile synthesis:

General procedure: A mixture of benzylamine 1a (107.0 mg, 1.0 mmol), CuCl (5.0 mg, 0.05 mmol, 5 molpercent), 2,2,6,6-tetramethyl-1-piperidyloxy (TEMPO, 7.8 mg, 0.05 mmol, 5 molpercent), and N,N-dimethylethane-1,2-diamine (DMEDA, 4.4 mg, 0.05 mmol, 5 molpercent) in toluene (0.5 mL) sealed in a Schlenk tube (100 mL) with an air balloon was stirred at 80 °C for 24 h. The reaction was then monitored by TLC and/or GC-MS. After completion of the reaction, solvent was evaporated under vacuum. The residue was purified by scosh column chromatography on silica gel using petroleum ether and ethyl acetate (0–100/1) as the eluent, giving product 2a in 80percent isolated yield

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Rx-ID: 7246488 Find similar reactions

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Aventis Research and Technologies GmbH and Co KG

Patent: US6166242 A1, 2000 ; Title/Abstract Full Text Show Details

C.4:Preparation of 2-fluorobenzonitrile From 2-chlorobenzonitrile COMPARATIVE EXAMPLE 4 Preparation of 2-fluorobenzonitrile From 2-chlorobenzonitrile The procedure of Example 3 is repeated but without addition of nitrobenzene. Yield: 92percent Selectivity: 94percent Benzonitrile content: 0.35percent 91%

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Aventis Research and Technologies GmbH and Co KG

Patent: US6166242 A1, 2000 ; Title/Abstract Full Text Show Details

5:Preparation of 2-fluorobenzonitrile From 2-chlorobenzonitrile

EXAMPLE 5 Preparation of 2-fluorobenzonitrile From 2-chlorobenzonitrile The procedure of Example 3 is repeated but using 2.5 g of bis(4-nitrophenyl)ether in place of the nitrobenzene. Yield: 91 percent Benzonitrile content: 0.01 percent 77%

With oxygen; copper(II) trifluoroacetate in dimethyl sulfoxide

T=110°C; 26 h; Sealed tubeGreen chemistry; Hide Experimental Procedure

Huaqiao University; Song, Qiuling; Feng, Qiang

Patent: CN103772236 B, 2016 ; Location in patent: Paragraph 0021; 0022; 0023; 0054; 0055; 0056; 0057 ; Title/Abstract Full Text Show Details

12.1:

General procedure: phenylacetic acid or its derivative (0.5mmol), Cu(TFA)2(20mmolpercent), urea (1.5 mmol) was added to the pressure sealed tube containing (0.75mL) of DMSO, after filling oxygen at 130 stirred for about 20h, the process by TLC and GC tracking (specifically the reaction time is determined by GC and TLC tracking results). After the raw material was observed by the GC and TLC the reaction has been completed the reaction, the reaction was removed, cooled to room temperature.To the reaction was added 20mL of ethyl acetate, washed with NaHCO3(20mL × 2), washed with saturated brine 20mL.The combined aqueous phases with ethyl acetate (20mL × 2) after stripping the combined organic phases with anhydrous sodium sulfate. The organic phase was dried by rotary evaporator spin solvent, product was purified by silica gel column, eluent ratio of ethyl acetate: petroleum ether = 50: 1. Benzonitrile obtained in a yield of 84percent.

Luecke; Winter

Chimia, 1971 , vol. 25, p. 94 Full Text View citing articles Show Details

Ishikawa; Inoue

Yuki Gosei Kagaku Kyokaishi, 1969 , vol. 27, p. 993,996 Chem.Abstr., vol. 72, # 21417 Full Text Show Details

Spagnolo et al.

Journal of the Chemical Society [Section] B: Physical Organic, 1971 , p. 2006 Full Text View citing articles Show Details

Becke; Burger

Justus Liebigs Annalen der Chemie, 1968 , vol. 716, p. 78 Full Text Show Details

Crow; Wentrup

Tetrahedron Letters, 1968 , p. 5569 Full Text View citing articles Show Details

IHARA CHEMICAL INDUSTRY CO., LTD.

Patent: EP1555257 A1, 2005 ; Location in patent: Page/Page column 27 ; Title/Abstract Full Text Show Details

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Mallinckrodt, Inc.

Patent: US4849552 A1, 1989 ; Title/Abstract Full Text Show Details

The fluoroaromatic compounds resulting from carrying out the process of this invention using the illustrative chloroaromatic compounds (a) through (z) above are set forth below, followed by utilities for such resulting compounds: (a) 2-fluorobenzonitrile (b) 4-fluorobenzonitrile (c) 2-fluorobenzoyl chloride (d) 4-fluorobenzoyl chloride (e) 2-fluorobenzoyl fluoride ...

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Sandoz, Inc.

Patent: US4113727 A1, 1978 ; Title/Abstract Full Text Show Details

Again following the same procedure and using in place of benzonitrile an equivalent amount of ... (c) p-fluorobenzonitrile, (d) p-methylbenzonitrile, (e) p-methoxybenzonitrile, (f) m-fluorobenzonitrile, (g) o-fluorobenzonitrile, or (h) o-methylbenzonitrile, ENICHEM SYNTHESIS S.p.A.

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Patent: EP441004 A1, 1991 ; Title/Abstract Full Text Show Details

Examples of aromatic nitriles (I) which can be prepared by the process according to the present invention are: para-chloro-benzonitrile; meta-chloro-benzonitrile; ortho-chloro-benzonitrile; 2-fluoro-benzonitrile; 2,3-di-chloro-benzonitrile; 3,4-di-chloro-benzonitrile; 2,3,4-tri-chloro-benzonitrile; 2,4,5-tri-chloro-benzonitrile; 3,4,5-tri-chloro-benzonitrile; ...

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ENICHEM SYNTHESIS S.p.A.

Patent: EP441004 A1, 1991 ; Title/Abstract Full Text Show Details

Process according to claim 1, characterized in that the following nitriles (I) are prepared: para-chloro-benzonitrile; meta-chloro-benzonitrile; ortho-chloro-benzonitrile; 2-fluoro-benzonitrile; 2,3-di-chloro-benzonitrile; 3,4-di-chloro-benzonitrile; 2,3,4-tri-chloro-benzonitrile; 2,4,5-tri-chloro-benzonitrile; 3,4,5-tri-chloro-benzonitrile; ...

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MALLINCKRODT SPECIALTY CHEMICALS COMPANY

Patent: EP253838 B1, 1991 ; Title/Abstract Full Text Show Details

MALLINCKRODT SPECIALTY CHEMICALS COMPANY

Patent: EP253837 B1, 1991 ; Title/Abstract Full Text Show Details

MALLINCKRODT SPECIALTY CHEMICALS COMPANY

Patent: EP252964 B1, 1991 ; Title/Abstract Full Text Show Details

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Mitsui Chemicals, Inc.

Patent: US6242654 B1, 2001 ; Title/Abstract Full Text Show Details

...presented by the following formula (4) which can respectively correspond to the formula (1) can be obtained. (D) Fluorine substituted aromatic compound represented by the formula (4) corresponding to the hydroxy compound wherein X1 is a substituent of the group (a) in the formula(1): ... 2,6-diphenylfluorobenzene, 4-phenoxyfluorobenzene, 2-nitrofluorobenzene, 3-nitrofluorobenzene, 4-nitrofluorobenzene, 2,4-dinitrofluorobenzene, 2,5-dinitrofluorobenzene, 2,4,6-trinitrofluorobenzene, 2-cyanofluorobenzene, 3-cyanofluorobenzene, 4-cyanofluorobenzene, 2-chlorofluorobenzene, 3-chlorofluorobenzene, 4-chlorofluorobenzene, 2,4-dichlorofluorobenzene, 2,5-dichlorofluorobenzene,

2,6-dichlorofluorobenzene, 3,4-dichlorofluorobenzene, ... BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; DAHMANN, Georg; FIEGEN, Dennis; HANDSCHUH, Sandra; KLICIC, Jasna; LINZ, Guenter; SCHAENZLE, Gerhard; SCHNAPP, Andreas; EAST, Stephen P.; MAZANETZ, Michael Philip; SCOTT, John; WALKER, Edward

Patent: WO2011/92128 A1, 2011 ; Location in patent: Page/Page column 45 ; Title/Abstract Full Text Show Details

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Rx-ID: 38673589 Find similar reactions

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92%

With mesoporous silica SBA-15 supported Cu2O nanoparticles in N,N-dimethyl-formamide

T=120°C; 8 h; Green chemistry;

Yin, Wenzhu; Liu, Rui; He, Guangke; Lv, Wangjie; Zhu, Hongjun

RSC Advances, 2014 , vol. 4, # 71 p. 37773 - 37778 Title/Abstract Full Text View citing articles Show Details

42%

With 3 Pd/CeO2; sodium acetate in N,N-dimethylformamide; isopropyl alcohol

T=55°C; 10 h; Irradiation; Hide Experimental Procedure

Nanjing University of Technology; Guo, Cheng; Gong, Xubin; Wu, Lou; Li, Qing; Wang, Jianjiang

Patent: CN105777579 A, 2016 ; Location in patent: Paragraph 0042; 0043 ; Title/Abstract Full Text Show Details

13:Example 13: Photocatalytic synthesis of compound 2-fluorobenzonitrile

To a 25 mL screw test tube was added 0.25 mmol of 2-fluoroiodobenzene, 0.1 mmol of cyanide reagent K4 [Fe (CN) 6], sodium acetate 0 · 25 mmol, 100 mg 3 wtpercent Pd / CeO2, and then 7 mL of N, N-dimethylformamide and lmL isopropanol were mixed with Solvent to the test tube, 500W visible light irradiation under the magnetic stirring reaction, control visible light intensity of 0.64W / cm2, the reaction Temperature of 55 ° C, 10 hours after the reaction to stop the reaction, take a small amount of reaction solution by microporous membrane filtration, methanol solvent dilution The samples were tested in the liquid phase. The samples to be tested were compared with the 2-fluoroiodobenzene standard and the 2-fluorobenzonitrile standard. The conversion of the reaction substrate was 46.2percent, the selectivity of the target product was 100percent, and the liquid product yield was 46.2percent. Post-processing Method for washing with a cloth funnel filter catalyst, drying for recycling use; reaction solution by dichloromethane and water mixture After the solution was extracted, the organic layer was concentrated and the final product 2-fluorobenzonitrile was obtained by column chromatography. The yield was 42percent

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Rx-ID: 43101109 Find similar reactions

58%

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With tert.-butylhydroperoxide; copper(l) iodide in N,N-dimethylformamide

T=130°C; 24 h; Hide Experimental Procedure

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Qi, Chaorong; Hu, Xiaohan; He, Haitao

Synlett, 2016 , vol. 27, # 13 art. no. ST-2016-W0122-L, p. 1979 - 1982 Title/Abstract Full Text View citing articles Show Details

General procedure for the preparation of substituted benzonitriles (3a-3u)

General procedure: To a 25 mL round flask was added the mixture of boronic acid (1) (0.3 mmol), ethyl2-cyano-3-ethoxyacrylate (2a, 0.6 mmol), CuI (0.3 mmol), t-BuOOH (0.6 mmol) in DMF (2 mL)successively. The mixture was stirred at 130 °C for 24 h under air. After the reaction was completed, themixture was cooled to room temperature, diluted with water (15 mL) and then extracted withdichloromethane (5 mL × 3). The organic extract was washed with H2O (10 mL × 3) and dried overanhydrous Na2SO4. After removal of the CH2Cl2 in vacuum, the crude product thus obtained was purified bycolumn chromatography on silica gel using petroleum ether/ethyl acetate as eluent to give the desired product3

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Rx-ID: 43101141 Find similar reactions

69%

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With tert.-butylhydroperoxide; copper(l) iodide in N,N-dimethylformamide

T=130°C; 24 h;

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Qi, Chaorong; Hu, Xiaohan; He, Haitao

Synlett, 2016 , vol. 27, # 13 art. no. ST-2016-W0122-L, p. 1979 - 1982 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 41405954 Find similar reactions

86%

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With palladium diacetate; sodium carbonate; (1,3-bis(2,6diisopropylphenyl)-4,5-dihydro-1Himidazol-2-ylidene)·HCl in DMAA

T=120°C; 5 h; Hide Experimental Procedure

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Xu, Zhicheng; Xiao, Yunqing; Ding, Hong; Cao, Changsheng; Li, Haitao; Pang, Guangsheng; Shi, Yanhui

Synthesis (Germany), 2015 , vol. 47, # 11 art. no. SS-2014-F0771-OP, p. 1560 - 1566 Title/Abstract Full Text View citing articles Show Details

Mono-Cyanation; General Procedure

General procedure: To a vial (8 mL) were added Pd(OAc)2 (112 mg, 0.05 mmol), NHC 2(213 mg, 0.05 mmol), K4[Fe(CN)6]·3H2O (528 mg, 1.25 mmol), Na2CO3(530 mg, 5 mmol), and an aryl halide (5 mmol) under aerobic conditions.The mixture was stirred vigorously at 120 °C. Samples weretaken from the reaction mixture periodically, quenched with H2O, extractedwith EtOAc, and analyzed by GC–MS. After completion of thereaction, the mixture was allowed to cool to r.t., quenched with H2Oand extracted with EtOAc (3 × 15 mL). The combined extracts weredried (MgSO4) and the solvent was evaporated. The crude residue waspurified by column chromatography on silica gel (EtOAc–PE).

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With oxygen; cupric trifluoroacetate; urea in dimethyl sulfoxide

T=110°C; 26 h; Green chemistry;

Rx-ID: 37873188 Find similar reactions

Feng, Qiang; Song, Qiuling

Advanced Synthesis and Catalysis, 2014 , vol. 356, # 8 p. 1697 - 1702 Title/Abstract Full Text View citing articles Show Details

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A: 79% B: 6%

Stage #1: With n-butyllithium in tetrahydrofuran; hexane

T=-28°C; Flow reactor; Stage #2: With N-fluoro-N-(phenylsulfonyl)benzenesulfonamide in tetrahydrofuran; hexane

T=-28°C; Flow reactor; Reagent/catalyst;

Nagaki, Aiichiro; Uesugi, Yuki; Kim, Heejin; Yoshida, Jun-Ichi

Chemistry - An Asian Journal, 2013 , vol. 8, # 4 p. 705 - 708 Title/Abstract Full Text View citing articles Show Details

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B: 82%

Garcia-Alvarez, Rocio; Diaz-Alvarez, Alba E.; Crochet, Pascale; Cadierno, Victorio

RSC Advances, 2013 , vol. 3, # 17 p. 5889 - 5894 Title/Abstract Full Text View citing articles Show Details

With [Ru(η6C6Me6)Cl2(tris(dimethylamino)phosphine)]; hydroxylamine hydrochloride; sodium hydrogencarbonate in water

T=100°C; 7 h; Inert atmosphereSealed tubeGreen chemistry; Reagent/catalyst;

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A: 82% B: 10 %Spectr.

With copper(II)-modified 4Å molecular sieve in acetonitrile

T=80°C; 8 h;

Kiss, Arpad; Hell, Zoltan

Synthetic Communications, 2013 , vol. 43, # 13 p. 1778 - 1786 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h 1.2: 0.17 h 1.3: 14 h 2.1: 4,7,13,16,21,24-hexaoxa-1,10diazabicyclo[8.8.8]hexacosane*(18)FK; potassium carbonate / N,Ndimethyl-formamide; water / 0.05 h / 150 °C View Scheme

Rx-ID: 35885563 Find similar reactions

Chun, Joong-Hyun; Telu, Sanjay; Lu, Shuiyu; Pike, Victor W.

Organic and Biomolecular Chemistry, 2013 , vol. 11, # 31 p. 5094 - 5099 Title/Abstract Full Text View citing articles Show Details

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With 4,7,13,16,21,24-hexaoxa-1,10diazabicyclo[8.8.8]hexacosane*(18)FK; potassium carbonate in water; N,N-dimethyl-formamide

T=150°C; 0.0502778 h; Temperature;

Rx-ID: 35885567 Find similar reactions

Chun, Joong-Hyun; Telu, Sanjay; Lu, Shuiyu; Pike, Victor W.

Organic and Biomolecular Chemistry, 2013 , vol. 11, # 31 p. 5094 - 5099 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 29286878 Find similar reactions

A: 74%

With tetra-(n-butyl)ammonium iodide; triethylamine; bis(dibenzylideneacetone)-palladium(0); t-BuDPEphos in 1,4-dioxane

T=100°C; 24 h;

Murata, Miki; Sambommatsu, Tomoko; Oda, Takeshi; Watanabe, Shinji; Masuda, Yuzuru

Heterocycles, 2010 , vol. 80, # 1 p. 213 - 218 Title/Abstract Full Text View citing articles Show Details

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With 9,10-anthracenedione in N,N-dimethyl-formamide

8.25 h; Electrochemical reaction;

Rx-ID: 9312405 Find similar reactions

Efremova; Podryvanova; Vasil'eva; Starichenko; Shteingarts

Russian Journal of Organic Chemistry, 2003 , vol. 39, # 2 p. 212 - 218 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 5321507 Find similar reactions

85%

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With zinc; 1,1'-bis(diphenylphosphino)ferrocene; tris(dibenzylideneacetone)dipalladium (0) in N,N-dimethyl acetamide T=150°C; Substitution; 12 h;

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Jin, Fuqiang; Confalone, Pat N.

Tetrahedron Letters, 2000 , vol. 41, # 18 p. 3271 - 3273 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 24427562 Find similar reactions

94%

With potassium fluoride in sulfolane; nitrobenzene; chlorobenzene

Aventis Research and Technologies GmbH and Co KG

Patent: US6166242 A1, 2000 ;

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Title/Abstract Full Text Show Details

3:Preparation of 2-fluorobenzonitrile From 2-chlorobenzonitrile

EXAMPLE 3 Preparation of 2-fluorobenzonitrile From 2-chlorobenzonitrile 137.5 g (1 mol) of 2-chlorobenzonitrile, 58 g (1 mol) of potassium fluoride, 5 g of nitrobenzene, 7.98 g of tetrakis(diethylamino)phosphonium bromide (phase transfer catalyst) and 30 ml of sulfolane are placed in a 500 ml four-neck flask fitted with thermometer, anchor stirrer and reflux condenser with bubble counter. The mixture is subsequently heated while stirring to 190° C. and allowed to react for 20 hours. After the reaction is complete, the reaction mixture is allowed to cool, dissolved in chlorobenzene, insoluble constituents are filtered off and the product (2-fluorobenzonitrile) is purified by fractional distillation under reduced pressure. Yield: 94percent Selectivity: 96percent Benzonitrile content: 0.1 percent

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Rx-ID: 24427563 Find similar reactions

90%

With potassium fluoride in sulfolane; chlorobenzene

Hide Experimental Procedure

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Aventis Research and Technologies GmbH and Co KG

Patent: US6166242 A1, 2000 ; Title/Abstract Full Text Show Details

11:Preparation of 2-fluorobenzonitrile From 2-chlorobenzonitrile

EXAMPLE 11 Preparation of 2-fluorobenzonitrile From 2-chlorobenzonitrile 137.5 g (1 mol) of 2-chlorobenzonitrile, 58 g (1 mol) of potassium fluoride, 5 g of phenyl methyl sulfoxide, 7.98 g of tetrakis(diethylamino)phosphonium bromide (phase transfer catalyst) and 30 ml of sulfolane are placed in a 500 ml four-neck flask fitted with thermometer, anchor stirrer and reflux condenser with bubble counter. The mixture is subsequently heated while stirring to 190° C. and allowed to react for 20 hours. After the reaction is complete, the reaction mixture is allowed to cool, dissolved in chlorobenzene, insoluble constituents are filtered off and the product (2-fluorobenzonitrile) is purified by fractional distillation under reduced pressure. Yield: 90percent Selectivity: 93percent Benzonitrile content: 0.08percent

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Hide Experimental Procedure

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Rx-ID: 24970276 Find similar reactions

Allied-Signal Inc.

Patent: US5081275 A1, 1992 ; Title/Abstract Full Text Show Details

3:EXAMPLE 3

EXAMPLE 3 This Example is directed to the preparation of 2-fluorobenzonitrile in solvent by using the product of Example 2. 15 milliliters sulfolane, 3.2 grams(0.055 mole) spray-dried potassium fluoride, and 10.2 grams(0.055 mole) of the 2-cyanobenzenesulfonyl fluoride prepared in Example 2 above were heated under nitrogen at 250° C. for one hour. The product was distilled directly from the resultant reaction mixture; the product weighed 5.6 grams and was identified by infrared spectroscopy as 2-fluorobenzonitrile. Based on 2-cyanobenzenesulfonyl fluoride, the per cent yield of 2-fluorobenzonitrile was 84. With potassium fluoride

Allied-Signal Inc.

Patent: US5081275 A1, 1992 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

4:EXAMPLE 4

EXAMPLE 4 This Example is directed to the preparation of 2-fluorobenzonitrile in the absence of solvent by using the product of Example 2. A mixture of 3.2 grams(0.055 mole) potassium fluoride, 10.2 grams(0.055 mole) of 2-cyanobenzenesulfonyl fluoride prepared in Example 2 above, and 0.1 gram dibenzo-18-crown-6 was stirred and heated under nitrogen at 225°-245° C. for two hours. The product was then vacuum distilled from the reaction mixture and weighed 2.9 grams. Based on 2-cyanobenzenesulfonyl fluoride, the per cent yield of 2-fluorobenzonitrile was 44. A

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in N,N-dimethyl-formamide

kfr; Rate constant;

Efremova, N. V.; Starichenko, V. F.; Shteingarts, V. D.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, p. 47 - 56 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 1 p. 57 - 68 Title/Abstract Full Text Show Details

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With Rb(18)F in dimethyl sulfoxide

T=150°C; 0.333333 h;

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Rx-ID: 3569595 Find similar reactions

Attina, Marina; Cacace, Fulvio; Wolf, A. P.

Journal of the Chemical Society, Chemical Communications, 1983 , # 3 p. 108 - 109 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1710038 Find similar reactions

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So, Y. H.; Miller, Larry L.

Journal of the American Chemical Society, 1981 , vol. 103, # 14 p. 4204 - 4209 Title/Abstract Full Text View citing articles Show Details

gaseous plasma of glow discharge; Yield given. Yields of byproduct given;

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Rx-ID: 1710040 Find similar reactions

So, Y. H.; Miller, Larry L.

Journal of the American Chemical Society, 1981 , vol. 103, # 14 p. 4204 - 4209 Title/Abstract Full Text View citing articles Show Details

gaseous plasma of glow discharge; Yield given. Yields of byproduct given;

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With cobalt (III) fluoride in chloroform

18 h; Heating; Product distribution;

Zweig, Arnold; Fischer, Robert G.; Lancaster, John E.

Journal of Organic Chemistry, 1980 , vol. 45, # 18 p. 3597 - 3603 Title/Abstract Full Text View citing articles Show Details

A: 62 % Chromat. B: 13 % Chromat. C: 27 % Chromat.

With fluorine in trichlorofluoromethane

T=-78°C; 1 h; competitive reaction with benzene; Rate constantProduct distribution;

Cacace, F.; Giacomello, P.; Wolf, A. P.

Journal of the American Chemical Society, 1980 , vol. 102, # 10 p. 3511 - 3515 Title/Abstract Full Text View citing articles Show Details

A: 0.7 % Spectr. B: 0.5 % Spectr. C: 0.9 % Spectr.

With CsSO4F in acetonitrile

T=25°C; reagents ratio, presence of 1,3,5-trinitrobenzene; Product distributionRate constant;

Ip, Dominic P.; Arthur, Carol D.; Winans, Randall E.; Appelman, Evan H.

Journal of the American Chemical Society, 1981 , vol. 103, # 8 p. 1964 - 1968 Title/Abstract Full Text View citing articles Show Details

A: 62 % Chromat. B: 13 % Chromat. C: 27 % Chromat.

With fluorine in trichlorofluoromethane

T=-78°C; 1 h;

Cacace, F.; Giacomello, P.; Wolf, A. P.

Journal of the American Chemical Society, 1980 , vol. 102, # 10 p. 3511 - 3515 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 20511075 Find similar reactions

Multi-step reaction with 2 steps 1: gaseous plasma of glow discharge 2: gaseous plasma of glow discharge View Scheme

So, Y. H.; Miller, Larry L.

Journal of the American Chemical Society, 1981 , vol. 103, # 14 p. 4204 - 4209 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: gaseous plasma of glow discharge 2: gaseous plasma of glow discharge View Scheme

So, Y. H.; Miller, Larry L.

Journal of the American Chemical Society, 1981 , vol. 103, # 14 p. 4204 - 4209 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 1710039 Find similar reactions

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B: 17 % Chromat. C: 14 % Chromat. D: 14 % Chromat. E: 4.0 % Chromat.

So, Ying-Hung; Miller, Larry L.

Journal of the American Chemical Society, 1980 , vol. 102, # 23 p. 7119 - 7120 Title/Abstract Full Text View citing articles Show Details

plasma apparatus; a variety of substituted benzenes and pyridine similarly cyanated; Product distribution;

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Synthesize Find similar Rx-ID: 2937808 Find similar reactions

A: 0.28 g B: 0.22 g C: 0.03 g D: 0.99 g

With caesium tetrafluorocobaltate(III)

T=300°C; 1.5 h; fluorination of benzonitriles over caesium tetrafluorocobaltate(III) at elevates temperatures; Product distribution;

Phull, Gurjeet S.; Plevey, Raymond G.; Rendell, Richard W.; Tatlow, John Colin

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980 , p. 1507 - 1511 Title/Abstract Full Text View citing articles Show Details

A: 0.28 g B: 0.22 g C: 0.03 g

With caesium tetrafluorocobaltate(III)

T=300°C; 1.5 h; Yields of byproduct given;

Phull, Gurjeet S.; Plevey, Raymond G.; Rendell, Richard W.; Tatlow, John Colin

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980 , p. 1507 - 1511 Title/Abstract Full Text View citing articles Show Details

With caesium tetrafluorocobaltate(III)

T=300°C; 1.5 h; Yield given. Yields of byproduct given;

Phull, Gurjeet S.; Plevey, Raymond G.; Rendell, Richard W.; Tatlow, John Colin

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980 , p. 1507 - 1511 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 6216107 Find similar reactions

With silver(II) fluoride in chloroform

18 h; Heating; Product distribution;

Zweig, Arnold; Fischer, Robert G.; Lancaster, John E.

Journal of Organic Chemistry, 1980 , vol. 45, # 18 p. 3597 - 3603 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 25405227 Find similar reactions

With KF in tetramethylene sulfide

Hide Experimental Procedure

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I.S. C. Chemicals Limited

Patent: US4209457 A1, 1980 ; Title/Abstract Full Text Show Details

3:EXAMPLE 3

EXAMPLE 3 A mixture of 2-chlorobenzonitrile, m.p. 93°, (200 g., 1.45 moles) and KF (99.9 g., 1.72 moles) in sulpholane (720 g., 5.85 moles) was kept at 240° for 20 hr. (slight reflux) in a 2 l. flanged flask fitted with a stainless steel stirrer, thermometer pocket and reflux condenser. The conversion of 2-chlorobenzonitrile (2ClBN) into 2-fluorobenzonitrile (2FBN) was 48percent after the first 9 hr. and 77percent after a total reaction time of 20 hr., according to g.l.c. analysis.

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Hide Experimental Procedure

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Rx-ID: 25340351 Find similar reactions

Nippon Kayaku Kabushiki Kaisha

Patent: US4124631 A1, 1978 ; Title/Abstract Full Text Show Details

33:EXAMPLE 33

EXAMPLE 33 The reaction described in Example 15 was carried out except that o-fluorotoluene was used in place of o-chlorotoluene. The contact time, the reaction temperature and the results were as follows. Contact time: 4.8 seconds Reaction temperature 440° C Conversion of o-fluoretoluene: 95.7percent Yield of o-fluorobenzonitrile: 84.7percent

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Rx-ID: 348179 Find similar reactions

Borsche; Wagner-Roemmich

Justus Liebigs Annalen der Chemie, 1941 , vol. 546, p. 273,275 Full Text View citing articles Show Details