Water → Methyl 3-bromo-5-(hydroxymethyl)benzoate

Participants

Reaction Steps

To a stirred solution of dimethyl 5-bromoisophthalate (5.4 g, 20 mmol) in methanol (300 mL) at 0° C. was slowly added sodium tetrahydroborate (10 g, 0.28 mol). The mixture was stirred at rt for 3 h, and then treated with water (300 mL). The volatiles were removed in vacuo and the aqueous phase was extracted with CH2Cl2 (100 mL×3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The resulting oil was purified by flash chromatography to afford the title compound.

Provenance & Evidence