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

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 4-bromo-3-methylbenzoate (50.0 g, 218 mmol), lithium tetrahydroborate (5.70 g, 262 mmol) and tetrahydrofuran (500 mL) was stirred at 25° C. for 2 d. The reaction was cooled to 0° C., quenched with saturated NH4Cl solution and diluted with ethyl acetate. The aqueous layers were extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (36.0 g, 82%).

Provenance & Evidence