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-46fb0345363741fea4ca7925d20d1fc2

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173810B2