Bromoform → 1,1-Dibromo-2-(3,4-dichlorophenyl)cyclopropane
Reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH2:16])[CH:11]=[CH:12][C:13]=1[Cl:14].[CH:17]([Br:20])(Br)[Br:18]>O>[Br:18][C:17]1([Br:20])[CH2:16][CH:15]1[C:10]1[CH:11]=[CH:12][C:13]([Cl:14])=[C:8]([Cl:7])[CH:9]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
Potassium t-butoxide (5.1 g.) was added to a stirred mixture of 3,4-dichlorophenylethylene (6.1 g.), bromoform (8.9 g.) and petroleum ether (b.p. 60°-80° C.; 100 ml.) which was cooled to -30° C., and the mixture was stirred at that temperature for 30 minutes, then at laboratory temperature for 17 hours and then poured into water. The mixture was extracted with ethyl acetate and the extract was washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and evaporated to dryness under reduced pressure The residue was purified by chromatography on a silica gel column using petroleum ether (b.p. 40°-60° C.) as eluant, and there was thus obtained as an oil 1,1-dibromo-2-(3,4-dichlorophenyl)cyclopropane.
Workup
- waitat laboratory temperature for 17 hours
- extractionThe mixture was extracted with ethyl acetate
- washthe extract was washed with saturated aqueous sodium chloride solution
- dry with materialdried over magnesium sulphate
- customevaporated to dryness under reduced pressure The residue
- customwas purified by chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-b66594a2a8b5460c85a003e5be7a552e
- Source dataset
- uspto-grants-1991_07
- Patent number
- US05032592
Reaction notes
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