Hydrochloric Acid → 1,1,1-Trifluoro-2-(4-methoxyphenyl)propan-2-ol

A solution of 1-bromo-4-methoxybenzene (19 ml, 150 mmol) in 300 ml of dry THF at −78° C. was treated with n-butyllithium (96 ml, 154 mmol) (1.6 M or 15% in hexanes, Strem). The resulting mixture was stirred for an additional 30 min. At −78° C., 1,1,1-trifluoropropan-2-one (16 ml, 180 mmol) was added and the mixture was stirred −78° C. and slowly warmed up overnight. The reaction mixture was treated with 100 ml of 5N HCl and concentrated. The layers were separated. The bottom layer (organic) was diluted with 50 ml of DCM, washed with 1×100 ml of H2O, and dried (MgSO4) and concentrated to give an oil which was purified by silica gel chromatography eluting with 0-5% EtOAc in hexanes to provide the title compound.

1. stirringthe mixture was stirred −78° C.
2. temperatureslowly warmed up overnight
3. concentrationconcentrated
4. customThe layers were separated
5. additionThe bottom layer (organic) was diluted with 50 ml of DCM
6. washwashed with 1×100 ml of H2O
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customto give an oil which
10. customwas purified by silica gel chromatography
11. washeluting with 0-5% EtOAc in hexanes

ORD record

ord-61457c6f5dc14bae8df6ecbfc2dae271

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633315B2