1,2-Dibromoethane → Methyl 3-(1-cyanocyclopropyl)benzoate

Participants

Reaction Steps

To a solution of methyl 3-(cyanomethyl)benzoate (1.5 g, 8.6 mmol) in dimethyl sulfoxide (30 mL) was added sodium hydride (60% in oil, 1.0 g, 26 mmol) while cooling the solution to a temperature of 25° C. or below at which the solution did not solidify. The reaction mixture was stirred at room temperature for 30 min, 1,2-dibromoethane (2.4 g, 12.8 mmol) was added, and the mixture was further stirred at room temperature for 10 hr. The reaction mixture was diluted with water (100 mL), and extracted with ethyl acetate (300 mL). The organic layer was washed with saturated brine (100 mL), and dried over anhydrous sodium sulfate, and the insoluble material was filtered off. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→50/50), and fractions containing the object product was concentrated under reduced pressure to give the title compound (1.3 g, 76%) as a colorless oil.

Provenance & Evidence