Borane;tetrahydrofuran → (4-Bromo-3-(trifluoromethyl)phenyl)methanol

To a solution of 4-bromo-3-(trifluoromethyl)benzoic acid 46-2 (1.35 g, 5 mmol) in THF (10 mL) was added 1M BH3.THF in THF (20 mL) slowly at 0° C. The mixture was warmed up to room temperature and stirred for 4 hours. The reaction was quenched with water at 0° C. All the solvents were evaporated and the residue was redissolved in ethyl acetate (100 mL), washed with saturated NaHCO3 aqueous solution, water and brine, dried over Na2SO4, and then concentrated. The crude product was purified by silica gel flash chromatography, eluted with 40% ethyl acetate in hexane to give (4-bromo-3-(trifluoromethyl)phenyl)methanol 46-3 as white solid. MS m/z 237.1 (M+1)

1. customThe reaction was quenched with water at 0° C
2. customAll the solvents were evaporated
3. dissolutionthe residue was redissolved in ethyl acetate (100 mL)
4. washwashed with saturated NaHCO3 aqueous solution, water and brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. customThe crude product was purified by silica gel flash chromatography
8. washeluted with 40% ethyl acetate in hexane

ORD record

ord-108c546b80b64ecba3619fd5bf3c5b78

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238646B2