Hydrochloric Acid → 3-Bromo-5-hydroxybenzenemethanol

To a solution of 3-bromo-5-hydroxy-benzoic acid (5.0 g, 23.4 mmol) in 40 mL of THF was added a solution of 1M LiAlH4 (30 mL), and the resulting solution was heated to reflux for 2 h. After cooling to room temperature, the reaction mixture was poured on ice and acidified with 10% aq. HCl. The solution was then filtered under vacuum and the filtrate was extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material was purified by column chromatography (Isco™ 120 g) using 50% ethyl acetate/hexanes as eluting solvents to afford the title compound as a white solid (1.7 g, 36% yield). HR-ES(−) calcd for C7H7O2Br [M−H]− 200.9556, observed 200.9557.

1. temperaturethe resulting solution was heated
2. temperatureto reflux for 2 h
3. additionthe reaction mixture was poured on ice
4. filtrationThe solution was then filtered under vacuum
5. extractionthe filtrate was extracted with EtOAc
6. extractionThe organic extract
7. dry with materialwas dried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe crude material was purified by column chromatography (Isco™ 120 g)
10. washas eluting solvents

ORD record

ord-0d08bb7fd2b14521a2d4adaec785907c

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088936B2