Sodium borohydride → 2-Bromo-5-(trifluoromethyl)benzyl alcohol

To a mixture of 2-bromo-5-(trifluoromethyl)benzaldehyde (5 g, 20 mmol) in THF (20 mL) at 0° C. was added sodium borohydride (0.8 g, 20 mmol). The resulting mixture was stirred at 0° C. to ambient temperature for 1 h. The reaction was quenched by addition of an aqueous solution of NaHCO3. The resulting solution was extracted with EtOAc twice. The combined extracts were washed with brine, dried (MgSO4), filtered and concentrated to give the desired alcohol as a white solid (4.4 g). 1H NMR (CDCl3) δ 7.81 (s, 1H), 7.66 (d, J=8.3 Hz, 1H), 7.42 (dd, J=8.3 Hz, 2.0 Hz, 1H), 4.81 (d, J=6.3 Hz, 2H), 2.03 (m, 1H).

1. customThe reaction was quenched by addition of an aqueous solution of NaHCO3
2. extractionThe resulting solution was extracted with EtOAc twice
3. washThe combined extracts were washed with brine
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-0e207ce3b4f0425b9b91844b1dfe1302

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268826B2