Borane;tetrahydrofuran → 6-Amino-3-bromo-2-fluorobenzenemethanol

To a solution of 6-amino-3-bromo-2-fluorobenzoic acid (9.0 g, 38.46 mmol) in THF (150 mL) was added BH3-THF (1 M, 193 mL) at 0° C., and the mixture was stirred at room temperature overnight. The reaction was slowly quenched with methanol (50 mL), and the solvents were removed under reduced pressure. The residue was diluted with 200 mL of ethyl acetate, washed with water (200 mL) and brine (200 mL), dried over sodium sulfate, filtered and concentrated to afford the title product (8.3 g, 98%), which was directly used in the next step without further purification. MS (ES+) C7H7BrFNO requires: 219, found: 220, 222 [M+H]+.

1. customThe reaction was slowly quenched with methanol (50 mL)
2. customthe solvents were removed under reduced pressure
3. additionThe residue was diluted with 200 mL of ethyl acetate
4. washwashed with water (200 mL) and brine (200 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-48efd38fab134ed9b2140e90274b5ab8

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434700B2