Potassium Carbonate → Methyl 3-cyano-4-(cyclopropylmethoxy)benzoate

Participants

Reaction Steps

A mixture of methyl 3-cyano-4-hydroxybenzoate (D22; 120 mg, 0.677 mmol), (bromomethyl)cyclopropane (Aldrich; 0.099 ml, 1.016 mmol), and potassium carbonate (140 mg, 1.016 mmol) in dry N,N-dimethylformamide (DMF) (2 ml) was heated under microwave irradiation at 150° for 90 mins. The cooled mixture was partitioned between water (30 ml) and ethyl acetate (3×25 ml), and the organic layer was washed with 50:50 brine:water and brine, dried (MgSO4) and evaporated in vacuo to give a light brown crystalline solid which was purified by flash chromatography on silica gel, eluting with 0-30% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white solid (74 mg)

Provenance & Evidence