4-Bromo-3-fluorobenzoic acid → (4-Bromo-3-fluorophenyl)methanol

A 0° C. solution of 4-bromo-3-fluoro benzoic acid (2.3 g, 10.50 mmol) in dry THF (52.5 ml) is treated with borane tetrahydrofuran complex (15.75 ml of a 1 M solution in THF, 15.75 mmol) and the resulting mixture stirred at RT for 72 hours. The mixture is then quenched with 1N HCl, stirred for 20 minutes, then extracted with DCM. Concentration and silica gel chromatography (10-50% EtOAc/hexanes) yields the title compound 1.87 g (87% yield) as colorless needles. 1H NMR (500 MHz, CDCl3) δ 7.55 (m, 1H), 7.04 (d, J 9.4 Hz, 1H), 7.04 (d, J 8.3 Hz, 1H), 4.70 (d, 2H).

1. customThe mixture is then quenched with 1N HCl
2. stirringstirred for 20 minutes
3. extractionextracted with DCM
4. concentrationConcentration and silica gel chromatography (10-50% EtOAc/hexanes)

ORD record

ord-af74ac6fc2424e6882c31e1434759b1e

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006228B2