2-(2-Bromo-5-fluorophenyl)acetic acid → 2-Bromo-5-fluorobenzeneethanol

To a solution of (2-bromo-5-fluorophenyl)acetic acid (1.29 g, 5.54 mmol) in tetrahydrofuran (15 mL) was added lithium aluminum hydride (210 mg, 5.54 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 3 h. After cooling to 0° C., the reaction mixture was quenched by the addition of 2N hydrochloric acid (30 mL), extracted with diethyl ether (200 mL). The organic layer washed with water (50 mL) and brine (50 mL) dried over magnesium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (40 g) eluting with hexane/ethyl acetate (5/1) to afford 247 mg (20%) of the title compound as colorless oil:

1. temperatureAfter cooling to 0° C.
2. customthe reaction mixture was quenched by the addition of 2N hydrochloric acid (30 mL)
3. extractionextracted with diethyl ether (200 mL)
4. washThe organic layer washed with water (50 mL) and brine (50 mL)
5. dry with materialdried over magnesium sulfate
6. customevaporated
7. customThe residue was purified by column chromatography on silica gel (40 g)
8. washeluting with hexane/ethyl acetate (5/1)

ORD record

ord-5e6e90c479f24f0a94d17b46a9882aaf

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354925B2