Acetonitrile → Methyl 3-(cyanomethyl)benzoate

Participants

Reaction Steps

To a solution of methyl 3-bromobenzoate (10.0 g, 44 mmol) in acetonitrile (100 mL) were added potassium cyanide (5.7 g, 87 mmol) and 18-crown-6 (1.0 g), and the mixture was stirred at room temperature for 3 days. The reaction mixture was filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→30/70), and the fraction containing the object product was concentrated under reduced pressure to give the title compound (7.0 g, 91%) as a colorless oil.

Provenance & Evidence