(Trifluoromethyl)trimethylsilane → 1-(4-Bromo-2-methylphenyl)-2,2,2-trifluoroethan-1-ol

To a solution of 4-bromo-2-methylbenzaldehyde (1.5 g, 7.5 mmol) in THF (20 mL) was added TMSCF3 (2.2 g, 15.5 mmol) at 0° C. and then TBAF (1.1 mL, 1.0 M in THF). The mixture was stirred at RT for 1 h, then diluted with HCl (3.0 M, 10 mL), stirred at RT for 1 h and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by normal phase silica gel column provided 1-(4-bromo-2-methylphenyl)-2,2,2-trifluoroethanol as an off-white solid.

1. stirringstirred at RT for 1 h
2. extractionextracted with ethyl acetate
3. washThe combined organic layer was washed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo
6. customPurification by normal phase silica gel column

ORD record

ord-2d7c2441c070452f9eab3b7f60dcc1fe

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199994B2