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 DMSO (30 mL) was added sodium hydride (60% in oil, 1.0 g, 26 mmol) while cooling the mixture to 25° C. or below to prevent precipitation. The reaction mixture was stirred at room temperature for 30 min, 1,2-dibromoethane (2.4 g, 12.8 mmol) was added thereto, 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 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 desired product were concentrated under reduced pressure to give the title compound (1.3 g, 76%) as a colorless oil.

Provenance & Evidence