5-Bromo-2-methoxyphenylacetic acid → 2-(5-Bromo-2-methoxyphenyl)ethan-1-ol

Participants

Reaction Steps

A solution of (5-bromo-2-methoxyphenyl)acetic acid (20.0 g, 81.6 mmol) in THF (400 mL) cooled to 0°, followed by dropwise addition of 1M BH3.THF in THF (122.4 mL, 122.4 mmol). After addition is complete, the solution is warmed to room temperature and stirring is continued for 1 hour. At this time, the reaction is cooled back to 0° and quenched with water (50 mL). The mixture is concentrated to 80 mL in vacuo, and the residue is extracted with EtOAc (3×150 mL). Te combined organic phase is washed with water (1×50 mL) and brine (1×50 mL), dried over MgSO4, and concentrated in vacuo to give 2-(5-bromo-2-methoxyphenyl)-1-ethanol.

Provenance & Evidence