5-Bromo-2-methylbenzoic acid → (5-Bromo-2-methylphenyl)methanol

Participants

Reaction Steps

To a solution of 5-bromo-2-methylbenzoic acid (25.00 g, 116 mmol) in THF (250 mL) at 0° C. was added borane dimethyl sulfide complex (2.0 M in THF, 87 mL, 174 mmol) dropwise. The reaction mixture was stirred at room temperature for 16 hours. The mixture was cooled to 0° C. and quenched by dropwise addition of MeOH (100 mL) within 15 minutes. The mixture was stirred at 0° C. for 15 minutes and concentrated. The residue was taken up in EtOAc and washed with 1 M HCl, saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated to give INT 29.

Provenance & Evidence