Borohydride → (2-Amino-5-bromo-3-fluorophenyl)methanol

To a solution of 2-amino-5-bromo-3-fluorobenzoic acid (14.5 g, 62.2 mmol) in THF (150 mL) at 0° C. was added borohydride in THF (1 M, 310 mL), and the reaction mixture was stirred at RT overnight. LCMS showed the reaction was completed. The reaction was quenched with methanol (150 mL), concentrated in vacuum, diluted with aqueous sodium bicarbonate (400 mL) and extracted with ethyl acetate (200 mL*3). The organic layers were separated, combined, washed with water (200 mL) and brine (200 mL), dried over sodium sulfate, filtered and concentrated to afford the title compound (13.0 g, crude), which was directly used in the next step without the further purification. MS (ES+) C7H7BrFNO requires: 219, 221. Found: 220, 222 [M+H]+.

1. customThe reaction was quenched with methanol (150 mL)
2. concentrationconcentrated in vacuum
3. additiondiluted with aqueous sodium bicarbonate (400 mL)
4. extractionextracted with ethyl acetate (200 mL*3)
5. customThe organic layers were separated
6. washwashed with water (200 mL) and brine (200 mL)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-c17ee2bb848b45c7b8b2c3d53f3c7579

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09126951B2