Acetic Acid → (4-Bromo-3-chlorophenyl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of BH3 (34 mL, IM in tetrahydrofuran) was added dropwise to the solution of 4-bromo-3-chlorobenzoic acid (2.5 g, 11.4 mmol) in tetrahydrofuran at 0° C. The mixture was stirred at 40° C. overnight. Acetic acid (5 mL) was added dropwise to the reaction mixture. The mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=1:1) to give (4-bromo-3-chlorophenyl)methanol as a white solid (4.47 g, 91%). 1H NMR (300 MHz, d6-DMSO): 7.69 (d, J=8.1, 1H), δ 7.53 (d, J=0.9, 1H), 7.19 (dd, J1=8.1, 1H J2=0.9, 1H), 5.38 (s, 1H), δ 4.48 (s, 2H).

Provenance & Evidence