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 was 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 was 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-102d4b84a82c4fd9b5a65cfaf1876a1a

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07279486B2