Water → (2-Bromo-5-methoxyphenyl)methanol

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Reaction Steps

5-Methoxy-2-bromobenzoic acid (85 g, 0.37 mol) is dissolved in anhydrous THF (100 mL) and cooled in an ice-salt bath until the temperature reaches −5° C. Borane-THF complex is added dropwise as a 1.0 M solution in THF (736 mL, 0.74 mol) at −5° C. After addition is complete, the reaction mixture is slowly warmed to room temperature and stirred for 12 hours. Water (40 mL) is slowly added dropwise and the reaction mixture stirred for 30 minutes. Additional water (350 mL) is added and the mixture is concentrated by rotary evaporator to remove most of the THF. The remaining material is extracted with EtOAc (800 mL). The organic layer is washed with saturated NaHCO3 (500 mL), brine (250 mL) and then dried (Na2SO4). Upon removal of the solvent by rotary evaporator, 5-methoxy-2-bromobenzyl alcohol is obtained as a white solid.

Provenance & Evidence