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

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.

1. additionAfter addition
2. temperatureAt this time, the reaction is cooled back to 0°
3. customquenched with water (50 mL)
4. concentrationThe mixture is concentrated to 80 mL in vacuo
5. extractionthe residue is extracted with EtOAc (3×150 mL)
6. washTe combined organic phase is washed with water (1×50 mL) and brine (1×50 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated in vacuo

ORD record

ord-97f593fd03c44ccd8dd697e09eaff988

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06291530B1