Boron tribromide → 5-Bromo-2-(1-hydroxy-2-methylpropan-2-yl)phenol

To a solution of 2-(4-bromo-2-methoxyphenyl)-2-methylpropan-1-ol (300 mg, 1.16 mmol) in dichloromethane (5 mL) was added dropwise boron tribromide (580 mg, 2.32 mmol) at −78° C. under nitrogen. The reaction mixture was warmed to room temperature and stirred for 30 minutes. The reaction was quenched with water (10 mL) and extracted with dichloromethane (20 mL). The organic layer was washed with aq. sodium bicaronate (20 mL), brine (20 mL), dried over sodium sulfate, filtered and concentrated to give a crude residue, which was purified by flash chromatography to give the title compound (90 mg, 32%) as a white solid.

1. customThe reaction was quenched with water (10 mL)
2. extractionextracted with dichloromethane (20 mL)
3. washThe organic layer was washed with aq. sodium
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a crude residue, which
8. customwas purified by flash chromatography

ORD record

ord-395146972f36469a85edfa39b4a33a25

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394285B2