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-c3f3ca882d0147dcbf92e714b8daf491

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680104B2