Query 1. Query
Query
Results
Date
IDE.XRN=1733962
70 reactions in Reaxys
2016-06-02 16h:40m:02s (EST)
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1/20
2016-06-02 16:43:58
Cl
O Cl
Si E
Br O
Si
Rx-ID: 32090738 View in Reaxys 1/70 Yield
Conditions & References
43 %
4.2. General procedure for the reaction of silylcyclopropyl bromides and dichloromethyl methyl ether with nBuLi General procedure: To a stirred solution of silylcyclopropyl bromide (1 mmol) in THF (20 mL) at -90 °C was added slowly a 1.6 M solution of n-BuLi (1.5 mL, 2.5 mmol) in hexane. The resulting reaction mixture was stirred at -90 °C for 0.3 h, and then dichloromethyl methyl ether (138 mg, 1.2 mmol) in THF (2 mL) was added. After stirring for 0.5 h, methanol (1 mL) was added and the reaction mixture was allowed to warm to ambient temperature and then poured into saturated NaHCO3 aq. The aqueous layer was extracted with diethyl ether for three times. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on a silica gel using 40:1 hexane/triethylamine as eluent to give methoxycyclopropylidenemethylsilane derivatives. Stage 1: With n-butyllithium in tetrahydrofuran, hexane, Time= 0.3h, T= -90 °C , Inert atmosphere Stage 2: in tetrahydrofuran, hexane, Time= 0.5h, T= -90 °C , Inert atmosphere Stage 3: With methanol in tetrahydrofuran, hexane, T= -90 °C , optical yield given as percent de Honda, Mitsunori; Nakae, Kenta; Nishizawa, Toshiaki; Suda, Mitsuhiro; Kunimoto, Ko-Ki; Segi, Masahito; Tetrahedron; vol. 67; nb. 49; (2011); p. 9500 - 9508 View in Reaxys
Cl
O
S
S
Cl O
Rx-ID: 24056209 View in Reaxys 2/70 Yield
Conditions & References
15%
55 : Preparation of benzothiophene-3-carboxaldehyde. Example 55 Preparation of benzothiophene-3-carboxaldehyde. Prepared by the Literature Procedure: J. Chem. Soc., 1969, 339-340 To a solution of benzothiophene (1.08 g, 8.0 mmol) in carbon disulfide (20 mL) at 0° C. was added titanium tetrachloride (3 mL, 27.3 mmol) followed by dichloromethyl n-butyl ether (1.24 g, 7.9 mmol) slowly dropwise. The reaction mixture was warmed to 25° C. and stirred for 1.5 h. The reaction was quenched with conc. hydrochloric acid solution (1 mL), diluted with chloroform (60 mL) and washed with water (50 mL), saturated sodium bicarbonate solution (2*30 mL) and brine (30 mL). The organic layer was dried (MgSO4), filtered, concentrated and flash chromatographed (silica gel, 2.5-5percent diethyl ether in petroleum ether) to afford benzothiophene-3-carboxaldehyde (195 mg, 15percent yield) as a yellow solid. With titanium tetrachloride in carbon disulfide, diethyl ether, Petroleum ether Patent; Fotouhi, Nader; Gillespie, Paul; Guthrie, Robert William; Pietranico-Cole, Sherrie Lynn; Yun, Weiya; US2002/161237; (2002); (A1) English View in Reaxys
Cl
O
O Cl
O P
O
O
Cl
Rx-ID: 25053227 View in Reaxys 3/70 Yield
Conditions & References 1 : Diethyl α-chloro-α-(n-butoxy)-methylphosphonate EXAMPLE 1
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2/20
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Diethyl α-chloro-α-(n-butoxy)-methylphosphonate A mixture of dichloromethyl butyl ether (13.5 g), triethyl phosphite (16.1 ml) and anhydrous zinc chloride (70 mg) was heated at 100° C. for 1 hour. Distillation in vacuo gave the title compound as a colourless oil. B.p. 93°-95° C. (0.15 mm Hg). NMR (CDCl3): δ=0.93 (t, 3H), 1.37 (t, 6H), 1.3-1.8 (m, 4H), 3.4-3.6 (m, 1H), 3.8-4.1 (m, 1H), 4.1-4.5 (m, 4H), and 5.65 (d, 1H) ppm. With triethyl phosphite, Zinc chloride Patent; Leo Pharmaceutical Products, Ltd.; US4732998; (1988); (A1) English View in Reaxys S S
Cl
O Cl O
Rx-ID: 1536575 View in Reaxys 4/70 Yield
Conditions & References
65 %
With tin(IV) chloride in dichloromethane, T= 10 °C Glaze, Alan P.; Harris, Stuart A.; Heller, Harry G.; Johncock, William; Oliver, Stephen N.; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 957 - 962 View in Reaxys
O
Cl
O
O
O O
O
O
O
Cl
O
O
O O
Rx-ID: 1917042 View in Reaxys 5/70 Yield
Conditions & References
70 %
With aluminium trichloride in chloroform, Time= 2h, T= 20 °C Verin, S. V.; Kuznetsov, E. V.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 28; nb. 2; (1992); p. 135 - 138; Khimiya Geterotsiklicheskikh Soedinenii; nb. 2; (1992); p. 169 - 172 View in Reaxys O
Cl
O Cl
Rx-ID: 1917043 View in Reaxys 6/70 Yield 59 %
Conditions & References With tin(IV) chloride in dichloromethane, Time= 2h, T= 20 °C Cerfontain, Hans; Koeberg-Telder, Ankie; Lerch, Ulrike; Recueil des Travaux Chimiques des Pays-Bas; vol. 112; nb. 11; (1993); p. 584 - 594 View in Reaxys
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3/20
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O
Cl
O Cl
Rx-ID: 4037845 View in Reaxys 7/70 Yield
Conditions & References With tin(IV) chloride in dichloromethane Boekelheide,V.; Sturm,E.; Journal of the American Chemical Society; vol. 91; (1969); p. 902 - 908 View in Reaxys With tin(IV) chloride Phillips,J.B. et al.; Journal of the American Chemical Society; vol. 89; nb. 7; (1967); p. 1704 - 1709 View in Reaxys O
O
Cl
O Cl
Rx-ID: 1917044 View in Reaxys 8/70 Yield
Conditions & References
51 %
With tin(IV) chloride in dichloromethane, Time= 2h, T= 20 °C Cerfontain, Hans; Koeberg-Telder, Ankie; Lerch, Ulrike; Recueil des Travaux Chimiques des Pays-Bas; vol. 112; nb. 11; (1993); p. 584 - 594 View in Reaxys
Cl
O O
Cl OH
OH
Rx-ID: 1917032 View in Reaxys 9/70 Yield
Conditions & References
90 %
With titanium tetrachloride in chloroform Andreeva, I. M.; Bondarenko, E. M.; Medyantseva, E. A.; Pudeyan, R. G.; Minkin, V. I.; Chemistry of Heterocyclic Compounds (New York, NY, United States); (1982); p. 455 - 458; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 5; (1982); p. 610 - 613 View in Reaxys O
Br
Cl
O Cl
O
O
E
O
O
Rx-ID: 3927306 View in Reaxys 10/70 Yield 99 %
Conditions & References With zinc in diethyl ether, Time= 0.333333h, Heating Lapkin, I. I.; Fotin, V. V.; Journal of Organic Chemistry USSR (English Translation); vol. 22; (1986); p. 659 - 663; Zhurnal Organicheskoi Khimii; vol. 22; nb. 4; (1986); p. 738 - 743 View in Reaxys
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4/20
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Cl
O
O Cl
racemate
Rx-ID: 4037846 View in Reaxys 11/70 Yield
Conditions & References With tin(IV) chloride in dichloromethane Boekelheide,V.; Sturm,E.; Journal of the American Chemical Society; vol. 91; (1969); p. 902 - 908 View in Reaxys
S
S
S
Cl
O
O
Cl
S
S
O
S
Rx-ID: 9061502 View in Reaxys 12/70 Yield
Conditions & References
48 %, 25 %
With titanium tetrachloride in dichloromethane, Time= 4h, T= -60 °C Kosata, Bedrich; Kozmik, Vaclav; Svoboda, Jiri; Collection of Czechoslovak Chemical Communications; vol. 67; nb. 5; (2002); p. 645 - 664 View in Reaxys O
O
Cl
O Cl
O
Rx-ID: 1702549 View in Reaxys 13/70 Yield
Conditions & References
84 %
With tin(IV) chloride in dichloromethane, Ambient temperature Sengupta, Dibyendu; Anand, Nitya; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 72 - 75 View in Reaxys O
Cl
O
O O
Br O
E
O
Cl
Rx-ID: 1885666 View in Reaxys 14/70 Yield
Conditions & References
81 %
With zinc in diethyl ether, Time= 0.333333h, Heating Lapkin, I. I.; Fotin, V. V.; Journal of Organic Chemistry USSR (English Translation); vol. 22; (1986); p. 659 - 663; Zhurnal Organicheskoi Khimii; vol. 22; nb. 4; (1986); p. 738 - 743 View in Reaxys
Cl
O Cl
O
Br
O
O
E
O
O
Rx-ID: 2922021 View in Reaxys 15/70 Yield 82 %
Conditions & References With zinc in diethyl ether, Time= 0.333333h, Heating Lapkin, I. I.; Fotin, V. V.; Journal of Organic Chemistry USSR (English Translation); vol. 22; (1986); p. 659 - 663; Zhurnal Organicheskoi Khimii; vol. 22; nb. 4; (1986); p. 738 - 743
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5/20
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View in Reaxys S
S
Cl
O O
Cl
Rx-ID: 1573056 View in Reaxys 16/70 Yield
Conditions & References
72 %
With tin(IV) chloride in dichloromethane, Time= 3h, Heating Krayushkin, M. M.; Loktionov, A. A.; Belen'kii, L. I.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 24; nb. 8; (1988); p. 850 - 856; Khimiya Geterotsiklicheskikh Soedinenii; vol. 24; nb. 8; (1988); p. 1034 1040 View in Reaxys O O
Cl
O
O
E
O
O
Cl
Br
Rx-ID: 1619654 View in Reaxys 17/70 Yield
Conditions & References
72 %
With zinc in diethyl ether, Time= 0.333333h, Heating Lapkin, I. I.; Fotin, V. V.; Journal of Organic Chemistry USSR (English Translation); vol. 22; (1986); p. 659 - 663; Zhurnal Organicheskoi Khimii; vol. 22; nb. 4; (1986); p. 738 - 743 View in Reaxys
O
Cl
O
O
O
Br O
O
O
Cl
O
Rx-ID: 1698946 View in Reaxys 18/70 Yield
Conditions & References
72 %
With zinc in diethyl ether, Time= 0.333333h, Heating Lapkin, I. I.; Fotin, V. V.; Journal of Organic Chemistry USSR (English Translation); vol. 22; (1986); p. 659 - 663; Zhurnal Organicheskoi Khimii; vol. 22; nb. 4; (1986); p. 738 - 743 View in Reaxys
O
Cl
O
HO
O–
O
O
Cl O
O
O+
O
Cl OO
Rx-ID: 1917037 View in Reaxys 19/70 Yield 70 %
Conditions & References With aluminium trichloride in chloroform, a) 0 deg C, b) r.t., 1 d Verin, S. V.; Kuznetsov, E. V.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 25; nb. 8; (1989); p. 866 - 868; Khimiya Geterotsiklicheskikh Soedinenii; nb. 8; (1989); p. 1039 - 1041 View in Reaxys
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6/20
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S
S
Cl
O Cl
O
Rx-ID: 1526384 View in Reaxys 20/70 Yield
Conditions & References
57 %
With tin(IV) chloride in dichloromethane, Time= 3h, Heating Krayushkin, M. M.; Loktionov, A. A.; Belen'kii, L. I.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 24; nb. 8; (1988); p. 850 - 856; Khimiya Geterotsiklicheskikh Soedinenii; vol. 24; nb. 8; (1988); p. 1034 1040 View in Reaxys S
S
Cl
O Cl
O
Rx-ID: 1553420 View in Reaxys 21/70 Yield
Conditions & References
55 %
With tin(IV) chloride in dichloromethane, Time= 3h, Heating Krayushkin, M. M.; Loktionov, A. A.; Belen'kii, L. I.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 24; nb. 8; (1988); p. 850 - 856; Khimiya Geterotsiklicheskikh Soedinenii; vol. 24; nb. 8; (1988); p. 1034 1040 View in Reaxys
O
O
Cl
O Cl
O
Rx-ID: 1804313 View in Reaxys 22/70 Yield
Conditions & References
58.3 %
With tin(IV) chloride in dichloromethane, Time= 0.75h, Ambient temperature Sengupta, Dibyendu; Anand, Nitya; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 72 - 75 View in Reaxys
Cl
O
O
O
O
Cl
Rx-ID: 1917040 View in Reaxys 23/70 Yield
Conditions & References With tin(IV) chloride in dichloromethane, Time= 10h, T= -78 °C , Title compound not separated from byproducts McCague, Raymond; Moody, Christopher J.; Rees, Charles W.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 2; (1984); p. 175 - 182 View in Reaxys With tin(IV) chloride in dichloromethane, T= -78 °C , Yield given. Yields of byproduct given McCague, Raymond; Moody, Christopher J.; Rees, Charles W.; Journal of the Chemical Society, Chemical Communications; nb. 9; (1982); p. 497 - 499 View in Reaxys
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7/20
2016-06-02 16:43:58
O
H N
HN
O
Cl
O Cl
O
Rx-ID: 4386737 View in Reaxys 24/70 Yield
Conditions & References With aluminium trichloride Phillips,J.B. et al.; Journal of the American Chemical Society; vol. 89; nb. 7; (1967); p. 1704 - 1709 View in Reaxys
O
Cl
O Cl
Rx-ID: 1008628 View in Reaxys 25/70 Yield
Conditions & References With tin(IV) chloride in dichloromethane, Ambient temperature Renfroe,H.B. et al.; Journal of Organic Chemistry; vol. 37; (1972); p. 3045 - 3052 View in Reaxys Br
OH
Cl
O O
Cl Br
OH
Rx-ID: 1917034 View in Reaxys 26/70 Yield
Conditions & References
31 %
With titanium tetrachloride in chloroform Andreeva, I. M.; Bondarenko, E. M.; Medyantseva, E. A.; Minkin, V. I.; Chemistry of Heterocyclic Compounds (New York, NY, United States); (1983); p. 146 - 149; Khimiya Geterotsiklicheskikh Soedinenii; vol. 19; nb. 2; (1983); p. 181 - 184 View in Reaxys
O
O
Cl
O Cl
Rx-ID: 1917039 View in Reaxys 27/70 Yield
Conditions & References With tin(IV) chloride in dichloromethane, Time= 0.75h, T= -78 °C , Yield given. Yields of byproduct given Gibbard, Howard C.; Moody, Christopher J.; Rees, Charles W.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 735 - 740 View in Reaxys
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8/20
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O
Cl
O
O
Cl O
Rx-ID: 4037847 View in Reaxys 28/70 Yield
Conditions & References With tin(ll) chloride in dichloromethane Klemm,L.H. et al.; Journal of Organic Chemistry; vol. 33; (1968); p. 1480 - 1488 View in Reaxys
O
O
Cl
S
O
O
Cl
S
S
O O
Rx-ID: 5320488 View in Reaxys 29/70 Yield
Conditions & References With titanium tetrachloride in dichloromethane, Time= 20h, T= 0 - 20 °C , Formylation, Title compound not separated from byproducts Pihera, Pavel; Svoboda, Jiri; Collection of Czechoslovak Chemical Communications; vol. 65; nb. 1; (2000); p. 58 76 View in Reaxys
O
Cl
O
O Cl
racemate
Rx-ID: 1008629 View in Reaxys 30/70 Yield
Conditions & References With tin(IV) chloride in dichloromethane, Ambient temperature Renfroe,H.B. et al.; Journal of Organic Chemistry; vol. 37; (1972); p. 3045 - 3052 View in Reaxys
O
O
Cl O
Cl
O Cl H
O
H
O
O
O
Rx-ID: 1008631 View in Reaxys 31/70 Yield
Conditions & References With aluminium trichloride in nitrobenzene Davis,B.R.; Watkins,W.B.; Tetrahedron; vol. 24; (1968); p. 2165 - 2175 View in Reaxys
O
C
Cl
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9/20
2016-06-02 16:43:58
Cl
Cl
Cl
O
O
O
Cl
Cl
Cl
Rx-ID: 5223571 View in Reaxys 32/70 Yield
Conditions & References With pyridine, tetrabutyl-ammonium chloride in acetonitrile, T= 24 °C , Ea; ΔS(excit.), Rate constant, Thermodynamic data Moss, Robert A.; Johnson, Lauren A.; Merrer, Dina C.; Lee Jr., George E.; Journal of the American Chemical Society; vol. 121; nb. 25; (1999); p. 5940 - 5944 View in Reaxys O
Cl
O
O
OH
Cl
Rx-ID: 11710886 View in Reaxys 33/70 Yield
Conditions & References Reaction Steps: 2 1: 99 percent / Zn filings / diethyl ether / 0.33 h / Heating 2: 80 percent / KOH / ethanol With potassium hydroxide, zinc in diethyl ether, ethanol Lapkin, I. I.; Fotin, V. V.; Journal of Organic Chemistry USSR (English Translation); vol. 22; (1986); p. 659 - 663; Zhurnal Organicheskoi Khimii; vol. 22; nb. 4; (1986); p. 738 - 743 View in Reaxys
Cl
O Cl O
Rx-ID: 1008626 View in Reaxys 34/70 Yield
Conditions & References With aluminium trichloride in dichloromethane Blackburn,E.V. et al.; Journal of the Chemical Society [Section] C: Organic; (1968); p. 1576 - 1580 View in Reaxys
O
Cl
O Cl
Rx-ID: 1008632 View in Reaxys 35/70 Yield
Conditions & References With titanium tetrachloride in dichloromethane Hoeffinger,J.-P. et al.; Bulletin de la Societe Chimique de France; (1970); p. 974 - 977 View in Reaxys O
Cl
O
O
OH
O O O
Cl
O
Rx-ID: 1231540 View in Reaxys 36/70 Yield
Conditions & References With triethylamine in 1,4-dioxane, diethyl ether
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10/20
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Gross,H.; Rieche,A.; Chemische Berichte; vol. 94; (1961); p. 538 - 543 View in Reaxys
Cl
O
O
O
O
Cl
O
N OH
O O
O
O O
N
N
O
O
O
Rx-ID: 1448004 View in Reaxys 37/70 Yield
Conditions & References With triethylamine in 1,4-dioxane, diethyl ether Gross,H.; Rieche,A.; Chemische Berichte; vol. 94; (1961); p. 538 - 543 View in Reaxys OH
Cl
O Cl OH
O
Rx-ID: 1917031 View in Reaxys 38/70 Yield
Conditions & References With titanium tetrachloride in chloroform Andreeva, I. M.; Babeshko, O. M.; Bondarenko, E. M.; Medyantseva, E. A.; Minkin, V. I.; Journal of Organic Chemistry USSR (English Translation); vol. 19; nb. 10; (1983); p. 1864 - 1869; Zhurnal Organicheskoi Khimii; vol. 19; nb. 10; (1983); p. 2146 - 2151 View in Reaxys
Cl
O O
Cl
Rx-ID: 4037844 View in Reaxys 39/70 Yield
Conditions & References With tin(IV) chloride in dichloromethane Campaigne,E.; Ashby,J.; Journal of Heterocyclic Chemistry; vol. 8; (1971); p. 487 - 488 View in Reaxys
Cl
O
O O
O
O
O
Cl
Rx-ID: 1008635 View in Reaxys 40/70 Yield
Conditions & References in dichloromethane Boekelheide,V. et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 1956 - 1959 View in Reaxys
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11/20
2016-06-02 16:43:58
Cl
O
O
O
O
O
Cl O
Rx-ID: 1008636 View in Reaxys 41/70 Yield
Conditions & References in dichloromethane Boekelheide,V. et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 1956 - 1959 View in Reaxys
O
Cl
O
O Cl
Rx-ID: 226410 View in Reaxys 42/70 Yield
Conditions & References With phosphorus pentachloride Laato; Suomen Kemistilehti B; vol. 32; (1959); p. 65; ; nb. 49; (1961); p. 35 View in Reaxys With phosphorus pentachloride Gross,H. et al.; Chemische Berichte; vol. 94; (1961); p. 544 - 550 View in Reaxys
S
O
S
Cl
O Cl
HN
HN
O
O
Rx-ID: 1788568 View in Reaxys 43/70 Yield 15 %
Conditions & References With titanium tetrachloride Bushkov, A. Ya.; Lantsova, O. I.; Bren', V. A.; Minkin, V. I.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 21; nb. 4; (1985); p. 476 - 477; Khimiya Geterotsiklicheskikh Soedinenii; vol. 21; nb. 4; (1985); p. 565 - 566 View in Reaxys
O O
S N
Cl
O
O
O Cl
S N
O
Rx-ID: 1827680 View in Reaxys 44/70 Yield
Conditions & References With aluminium trichloride Xu, Ru Xun; Anderson, Hugh J.; Gogan, Niall J.; Loader, Charles E.; McDonald, Robert; Tetrahedron Letters; vol. 22; nb. 49; (1981); p. 4899 - 4900 View in Reaxys
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12/20
2016-06-02 16:43:58
O
O
O
Br
Cl
O Cl O
H
H
O
O
Rx-ID: 1917036 View in Reaxys 45/70 Yield
Conditions & References With aluminium trichloride, water, 1.) nitrobenzene, 5 deg C, 124 h, 2.) reflux, Yield given. Multistep reaction Cambie, Richard C.; Metzler, Michael R.; Rickard, Clifton E. F.; Rutledge, Peter S.; Woodgate, Paul D.; Journal of Organometallic Chemistry; vol. 425; nb. 1-2; (1992); p. 59 - 87 View in Reaxys
Z
Z
Cl
O
O Cl
Rx-ID: 1917041 View in Reaxys 46/70 Yield
Conditions & References
13 %
With tin(IV) chloride Vogel, Emanuel; Schieb, Thomas; Schulz, Wolfgang H.; Schmidt, Klaus; Schmickler, Hans; Lex, Johann; Angewandte Chemie; vol. 98; nb. 8; (1986); p. 729 - 732 View in Reaxys Cl O
N Cl
N
O Cl Cl
Cl
Cl
O
O
Cl
Cl
N
N
O
Cl
Rx-ID: 5223578 View in Reaxys 47/70 Yield
Conditions & References in acetonitrile, Time= 0.333333h, T= 25 °C , Irradiation, other diazirines; also in the presence of pyridine or/and nBu4NCl, Product distribution Moss, Robert A.; Johnson, Lauren A.; Merrer, Dina C.; Lee Jr., George E.; Journal of the American Chemical Society; vol. 121; nb. 25; (1999); p. 5940 - 5944 View in Reaxys
Cl
Te
O
poly(o-phenylene)ditelluride
Cl
O Te
Rx-ID: 8486160 View in Reaxys 48/70 Yield
Conditions & References With sodium tetrahydroborate, 1) MeOH, 0 deg C; 2) MeOH, hexane, reflux, Yield given. Multistep reaction Sadekov, I. D.; Rivkin, B. B.; Gadzhieva, P. I.; Minkin, V. I.; Russian Chemical Bulletin; vol. 42; nb. 2; (1993); p. 350 - 351; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 2; (1993); p. 387 - 388 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
13/20
2016-06-02 16:43:58
O
O
P
Cl
Cl
O
O
Cl P
O
Cl
Cl
O Cl
Rx-ID: 913356 View in Reaxys 49/70 Yield
Conditions & References T= 110 - 120 °C Krut-skii,L.N. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 48; nb. 4; (1978); p. 780 - 783,713 - 715 View in Reaxys
Cl
O Cl O
Rx-ID: 1008627 View in Reaxys 50/70 Yield
Conditions & References With titanium tetrachloride Hoeffinger,J.-P. et al.; Bulletin de la Societe Chimique de France; (1969); p. 3099 - 3100 View in Reaxys
Cl
O
O
O
P
Cl
O
Cl
Cl P
O
Cl
O Cl
Rx-ID: 1238468 View in Reaxys 51/70 Yield
Conditions & References T= 110 - 120 °C Krut-skii,L.N. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 48; nb. 4; (1978); p. 780 - 783,713 - 715 View in Reaxys
O O
Cl
O
Z O
Cl
O
O
O
O HO
O
O
O O–
O–
O
O O+
O
Cl OO
O O
Cl O OO O+
OH O
Rx-ID: 1843934 View in Reaxys 52/70 Yield
Conditions & References With aluminium trichloride, perchloric acid, 1) methylene chloride, 2 days, Multistep reaction. Yields of byproduct given Shcherbakova, I. V.; Dorofeenko, G. N.; Kuznetsov, E. V.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 17; nb. 3; (1981); p. 221 - 224; Khimiya Geterotsiklicheskikh Soedinenii; vol. 17; nb. 3; (1981); p. 313 - 316 View in Reaxys With aluminium trichloride, perchloric acid, 1) methylene chloride, 2 days, Yield given. Multistep reaction
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Shcherbakova, I. V.; Dorofeenko, G. N.; Kuznetsov, E. V.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 17; nb. 3; (1981); p. 221 - 224; Khimiya Geterotsiklicheskikh Soedinenii; vol. 17; nb. 3; (1981); p. 313 - 316 View in Reaxys O
Cl
O
O
O
Cl
O
O
O
O
O O
Rx-ID: 1917035 View in Reaxys 53/70 Yield
Conditions & References With aluminium trichloride, water, 1.) CHCl3, 0 deg C, 30 min, 2.) CHCl3, 0 deg C, Yield given. Multistep reaction Tosunyan, D. E.; Berin, S. V.; Kuznetsov, E. V.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 28; nb. 11; (1992); p. 1249 - 1254; Khimiya Geterotsiklicheskikh Soedinenii; nb. 11; (1992); p. 1465 1471 View in Reaxys
Cl
O Br
Br
Cl
O
Rx-ID: 2946789 View in Reaxys 54/70 Yield
Conditions & References With tin(IV) chloride Matveentseva, M.S.; Buloichik, Zh.I.; Lazareva, A.M.; Uvarova, L.R.; Zyat'kov, I.P.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 741 - 744; Zhurnal Organicheskoi Khimii; vol. 20; nb. 4; (1984); p. 814 - 818 View in Reaxys
Cl
O
O
O
O
O
Cl HO
Rx-ID: 1008633 View in Reaxys 55/70 Yield
Conditions & References (i) CH2Cl2, (ii) NaBH4, MeOH, Multistep reaction Boekelheide,V. et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 1956 - 1959 View in Reaxys
Cl
O
OH O
O
O
O
Cl
Rx-ID: 1008634 View in Reaxys 56/70 Yield
Conditions & References (i) CH2Cl2, (ii) NaBH4, MeOH, Multistep reaction Boekelheide,V. et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 1956 - 1959 View in Reaxys
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O O
Cl
O
O O
O
Cl O HO O HO
O
O O–
O–
O
O O+
O
O
Cl OO
O
O O+
O
Cl OO
OH O
Rx-ID: 1917033 View in Reaxys 57/70 Yield
Conditions & References With aluminium trichloride, perchloric acid, 1) methylene chloride, 2 days, Yield given. Multistep reaction. Yields of byproduct given Shcherbakova, I. V.; Dorofeenko, G. N.; Kuznetsov, E. V.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 17; nb. 3; (1981); p. 221 - 224; Khimiya Geterotsiklicheskikh Soedinenii; vol. 17; nb. 3; (1981); p. 313 - 316 View in Reaxys
Cl
O Cl
Rx-ID: 1008623 View in Reaxys 58/70 Yield
Conditions & References (i) TiCl4, CS2, (ii) N2H4*H2O, EtOH, (iii) NaOH, HOCH2CH2OH, Multistep reaction Clar,E. et al.; Tetrahedron; vol. 25; (1969); p. 5639 - 5648 View in Reaxys
Cl
O Cl
Rx-ID: 1008624 View in Reaxys 59/70 Yield
Conditions & References (i) TiCl4, CS2, (ii) N2H4*H2O, EtOH, (iii) NaOH, diethylene glycol, Multistep reaction Clar,E. et al.; Tetrahedron; vol. 25; (1969); p. 5639 - 5648 View in Reaxys
Cl
O
O
Cl
Rx-ID: 1008625 View in Reaxys 60/70 Yield
Conditions & References (i) TiCl4, CS2, (ii) aq. HCl, Multistep reaction Clar,E. et al.; Tetrahedron; vol. 24; (1968); p. 2817 - 2823 View in Reaxys
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O
O O
Cl
O Cl H
H
O
O
O
O
Rx-ID: 1008630 View in Reaxys 61/70 Yield
Conditions & References (i) AlCl3, PhNO2, (ii) aq. NaHSO3, EtOH, Multistep reaction Davis,B.R.; Watkins,W.B.; Tetrahedron; vol. 24; (1968); p. 2165 - 2175 View in Reaxys
O
Cl
O P
O
O
O Cl
Cl
Cl
Rx-ID: 22425596 View in Reaxys 62/70 Yield
Conditions & References Reaction Steps: 2 1: 110 - 120 °C Krut-skii,L.N. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 48; nb. 4; (1978); p. 780 - 783,713 - 715 View in Reaxys
Cl
O
O O
Cl
O P
Cl
O
Cl
Rx-ID: 22425597 View in Reaxys 63/70 Yield
Conditions & References Reaction Steps: 2 1: 110 - 120 °C Krut-skii,L.N. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 48; nb. 4; (1978); p. 780 - 783,713 - 715 View in Reaxys
Cl
O
O
Cl
Rx-ID: 1366547 View in Reaxys 64/70 Yield
Conditions & References (i) TiCl4, CS2, (ii) aq. HCl, Multistep reaction Reimlinger,H. et al.; Chemische Berichte; vol. 97; (1964); p. 349 - 362 View in Reaxys
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-1 (v1)
O
2
Cl O
O
Cl
O
O
O
O
Cl O
O
O O
O+
O O
O +O
O
Rx-ID: 1917038 View in Reaxys 65/70 Yield
Conditions & References 1.) aluminium chloride, dichloromethane, 30 min, 0 deg C, 2.) 20 dec C, 1 h, 3.) nitromethane, 70percent perchloric acid, heating., Yield given. Multistep reaction Dulenko, V. I.; Nikolyukin, Yu. A.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 23; nb. 5; (1987); p. 493 - 495; Khimiya Geterotsiklicheskikh Soedinenii; vol. 23; nb. 5; (1987); p. 600 - 602 View in Reaxys
Cl
O Cl
O
O O
Rx-ID: 4120769 View in Reaxys 66/70 Yield
Conditions & References (i) TiCl4, CS2, (ii) aq. HCl, Multistep reaction Buu-Hoi,N.P. et al.; Bulletin de la Societe Chimique de France; (1968); p. 627 - 631 View in Reaxys
O
Cl
O O
F
F
O
H N
I
Cl
F
NH 2
F
F O
F
H N
H N
F F
N
O
O F
N H
O
O
F
O F
F
Rx-ID: 27973321 View in Reaxys 67/70 Yield
Conditions & References Multistep reaction. Shishido, Yuji; Wakabayashi, Hiroaki; Koike, Hiroki; Ueno, Naomi; Nukui, Seiji; Yamagishi, Tatsuya; Murata, Yoshinori; Naganeo, Fumiharu; Mizutani, Mayumi; Shimada, Kaoru; Fujiwara, Yoshiko; Sakakibara, Ayano; Suga, Osamu; Kusano, Rinko; Ueda, Satoko; Kanai, Yoshihito; Tsuchiya, Megumi; Satake, Kunio; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7193 - 7205 View in Reaxys
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O
Cl
O O
F
F
O
I
Cl
F
F
F
F F OF
O O
F
F
F
O
F
F O
F
OF
O
O
O
O
O O
Rx-ID: 27973322 View in Reaxys 68/70 Yield
Conditions & References Multistep reaction. Further byproducts. Shishido, Yuji; Wakabayashi, Hiroaki; Koike, Hiroki; Ueno, Naomi; Nukui, Seiji; Yamagishi, Tatsuya; Murata, Yoshinori; Naganeo, Fumiharu; Mizutani, Mayumi; Shimada, Kaoru; Fujiwara, Yoshiko; Sakakibara, Ayano; Suga, Osamu; Kusano, Rinko; Ueda, Satoko; Kanai, Yoshihito; Tsuchiya, Megumi; Satake, Kunio; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7193 - 7205 View in Reaxys
Cl
O Cl
Rx-ID: 6950750 View in Reaxys 69/70 Yield
Conditions & References Ameisensaeure-butylester, PCl5 <zunaechst unter Kuehlung, dann 15 min, 60grad> Rieche et al.; Chemische Berichte; vol. 93; (1960); p. 88,90 View in Reaxys (yield)58percent Rieche et al.; Chemische Berichte; vol. 93; (1960); p. 88,90 View in Reaxys Brenzcatechin-dichlormethylenether, Butylformiat <HgCl2, 25 min 100grad> Gross et al.; Justus Liebigs Annalen der Chemie; vol. 675; (1964); p. 142,150 View in Reaxys (yield)76percent Gross et al.; Justus Liebigs Annalen der Chemie; vol. 675; (1964); p. 142,150 View in Reaxys Ameisensaeure-butylester, Brenzcatechyl-phosphortrichlorid <0.5 h, 50 - 60grad> Gross; Gloede; Chemische Berichte; vol. 96; (1963); p. 1387,1391 View in Reaxys HCOOBu, /BRN= 743959/ Patent; Deutsche Akademie d. Wissenschaften zu Berlin; GB1005647; (1963); ; vol. 64; nb. 1954h; (1966) View in Reaxys Ameisensaeurebutylester, /BRN= 743959/ (100grad) Patent; Dt. Akad. Wiss.; DE1443704; (1969); ; vol. 72; nb. 54358; (1970) View in Reaxys
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Cl
O Cl
Rx-ID: 6756365 View in Reaxys 70/70 Yield
Conditions & References Rk. m. 2 zu 14 bzw. 24 u. 15 Renfroe,H.B. et al.; Journal of Organic Chemistry; vol. 37; (1972); p. 3045 - 3052 View in Reaxys Rk. m. 19 zu 20 Renfroe,H.B. et al.; Journal of Organic Chemistry; vol. 37; (1972); p. 3045 - 3052 View in Reaxys Rk. mit arom. Kohlenwasserstoffen, Methylenchlorid oder Schwefelkohlenstoff i. Ggw. von AlCl3, TiCl4 oder SnCl4 > Aldehyde, z. B. Phenanthren -> γ-Formyl-phenanthren; Veratrol -> Veratrumaldehyd, Anisol -> o- und p-Methoxybenzaldehyd Rieche et al.; Chemische Berichte; vol. 93; (1960); p. 88,90 View in Reaxys Umsetzung mit Essigsaeure, Triethylamin, Diethylether -> Diacetoxymethyl-butylether; reagiert analog mit anderen Carbonsaeuren Gross,H.; Rieche,A.; Chemische Berichte; vol. 94; (1961); p. 538 - 543 View in Reaxys
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