4-(Bromomethyl)benzoic acid → 4-(Bromomethyl)benzyl alcohol

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-bromomethylbenzoic acid (5.04; 23.3 mmol) in THF (30 ml) was cooled to 0° C. and treated with borane/THF (35 mmol). The ice bath was removed and the mixture was allowed to warm to room temperature and stirred for 1.5 hours. The excess borane was quenched with MeOH, and then with water, and the reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with 4% HCl, water NaHCO3, brine, dried (MgSO4), filtered, concentrated in vacuo to afford 4.44 g (94%) of the title compound.

Provenance & Evidence