Propylene Oxide → 2-Chloro-α-methyl-6-(trifluoromethyl)benzeneethanol

To a solution of 1-chloro-3-(trifluoromethyl)benzene (1.0 g, 5.5 mmol) in THF (10.0 mL) was added 2.5 M of n-BuLi in hexane (2.2 mL) at −78° C. and stirred for 1 h. Propylene oxide (370 mg, 6.4 mmol) was added to the reaction mixture at −78° C. and slowly warmed to rt. The reaction mixture was stirred for an additional 30 min. The reaction mixture was quenched with sat. aq. NH4Cl and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure to give a yellow oil. The material was purified by silica gel chromatography using Hexane/EtOAc (80:20) as eluent to yield the desired product as a yellow oil. 1H NMR (CDCl3, 400 MHz): δ=1.33 (d, J=6.1 Hz, 3H), 1.40 (d, J=6.3 Hz, 1H), 3.08-3.22 (m, 2H), 4.21-4.33 (m, 1H), 7.29-7.34 (m, 1H), 7.58-7.64 (m, 2H).

1. stirringThe reaction mixture was stirred for an additional 30 min
2. customThe reaction mixture was quenched with sat. aq. NH4Cl
3. extractionextracted with EtOAc
4. washThe organic layer was washed with brine
5. dry with materialdried over anhydrous Na2SO4
6. customthe solvent was removed under reduced pressure
7. customto give a yellow oil
8. customThe material was purified by silica gel chromatography

ORD record

ord-43f191c6cec74e208fc737dca5baffb1

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022206B2