Hydrochloric Acid → Methyl 4-fluorobenzimidate hydrochloride

Participants

Reaction Steps

Dry HCl (g) was bubbled through a solution of 4-fluorobenzonitrile (5.0 g, 0.041 mol) in dry MeOH—CH2Cl2 (20 mL, 1:1 v/v) until saturation. The clear solution was kept at 0° C. for 2 days to crystallize methyl 4-fluorobenzimidate as hydrochloride salt, which was isolated by filtration (2.8 g, yield 36%). 1H NMR (400 MHz, DMSO-d6) δ 7.95-7.92 (m, 2H), 7.38 (br s, 1H), 7.29-7.25 (m, 2H), 3.06 (s, 3H). MS (ESI) m/z: Calculated for C8H8FNO: 153.06. found: 154.2 (M+H)+.

Provenance & Evidence