Borane;tetrahydrofuran → (6-Amino-3-bromo-2-fluorophenyl)methanol
Reaction equation
[NH2:1][C:2]1[C:7]([C:8](O)=[O:9])=[C:6]([F:11])[C:5]([Br:12])=[CH:4][CH:3]=1.B.C1COCC1>C1COCC1>[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([F:11])[C:5]([Br:12])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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]+.