Methyl 4-bromo-3-methylbenzoate → (4-Bromo-3-methylphenyl)methanol

Participants

Reaction Steps

To a solution of methyl 4-bromo-3-methylbenzoate (500 mg, 2.18 mmol) in THF (5.2 mL) at −30° C. was slowly added LiAlH4 (83 mg, 2.18 mmol). The reaction mixture was stirred for 15 min, quenched with a solution of methanol and water (4:1, 10 mL), and stirred at rt for 30 min. The mixture was neutralized with 6 N HCl to pH of 7 and extracted with ethyl acetate (20 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to afford (4-bromo-3-methylphenyl)methanol (420 mg; yield 96%) as an oil.

Provenance & Evidence