Hydrochloric Acid → (5-Bromo-2-methylphenyl)methanol

Participants

Reaction Steps

Borane (10.80 mL of a 1M solution in THF, 10.80 mmol) was added to a cooled solution of 5-bromo-2-methyl-benzoic acid (116 mg, 0.54 mmol) in THF (15 mL), under nitrogen, at 0° C. (ice water bath) and the resulting mixture allowed to warm to rt overnight. The mixture was then treated with MeOH (10 mL) followed by aqueous HCl (2M, 20 mL) and the mixture stirred for about 15 minutes, concentrated under vacuum and then partitioned with EtOAc. The organic layer was washed with aqueous HCl (2M), water and brine, dried (MgSO4), filtered and reduced to give the title compound as a colourless oil (90 mg).

Provenance & Evidence