3-Cyanobenzoic acid → 3-(Hydroxymethyl)benzonitrile

Participants

Reaction Steps

3-Cyanobenzoic acid (5 g, 34.0 mmol) was dissolved in THF (50 mL) at ambient temperature. To this solution was added borane/THF complex (1M in THF, 68 mL, 68.0 mmol) in three portions and borane trifluoride/diethyl etherate complex (4.3 mL, 34.0 mmol). The reaction mixture was stirred at ambient temperature for 2 hours, quenched with methanol and stirred for 10 minutes. The solution was diluted with ethyl acetate and washed with saturated NaHCO3 (3×). The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo to give the title compound (2.19 g, 48% yield) as a solid.

Provenance & Evidence