2-Bromo-4-fluorophenylacetic acid → 2-(2-Bromo-4-fluorophenyl)ethan-1-ol

To a solution of (2-bromo-4-fluorophenyl)acetic acid (1.5 g, 6.44 mmol) in tetrahydrofuran (10 mL) was added 1M solution of borane-tetrahydrofuran complex in tetrahydrofuran (9.66 mL, 9.66 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 3 h. The reaction mixture was quenched by the addition of 2N hydrochloric acid (50 mL), extracted with ethyl acetate (200 mL). The organic layer washed with brine (50 mL) dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (5/1) to afford 1.30 g (92%) of the title compound as colorless oil:

1. customThe reaction mixture was quenched by the addition of 2N hydrochloric acid (50 mL)
2. extractionextracted with ethyl acetate (200 mL)
3. washThe organic layer washed with brine (50 mL)
4. dry with materialdried over sodium sulfate
5. customevaporated
6. customThe residue was purified by column chromatography on silica gel (100 g)
7. washeluting with hexane/ethyl acetate (5/1)

ORD record

ord-46264452ef1c4d3bbcc5fa1e437e51a9

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354925B2