Water → (4-Bromo-2-methylphenyl)methanol

Participants

Reaction Steps

Borane-dimethyl sulfide complex (2M in THF; 1150 mL, 2.3 mol) is added over 1.5 hours to a solution of 4-bromo-2-methylbenzoic acid (250 g, 1.16 mol) in anhydrous tetrahydrofuran (1500 mL) at 0° C. The reaction is allowed to warm slowly to ambient temperature and stirred overnight. The solution is cooled to −10° C. and water (500 mL) is added very slowly. Further water (5000 mL) is added and the mixture is extracted with ethyl acetate (2×5000 mL). The combined organic layers are washed with saturated aqueous NaCl solution (5000 mL) and dried over Na2SO4. Filtration and concentration under reduced pressure provides the title compound (226 g, 97% yield).

Provenance & Evidence