(Trifluoromethyl)trimethylsilane → 1-(3-Bromo-4-methylpyridin-2-yl)-2,2,2-trifluoroethanol

Temperature

-15 °C

Tetrabutylammonium fluoride (1.0 mol/L) in THF (1.2 mL, 1.20 mmol) was added dropwise to a solution of 3-bromo-4-methyl-pyridine-2-carbaldehyde (150 mg, 0.75 mmol), and (trifluoromethyl)trimethylsilane (2.0 mol/L) in THF (0.49 mL, 0.975 mmol) in THF (10 mL) cooled at −15° C. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (25 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue that was purified by flash chromatography (12 g, Silica, 0-30% ethyl acetate in heptane). Desired fractions were combined and evaporated in vacuo to afford the title compound as a white solid (90 mg, 44%), which was used in the next step without further purification.

1. temperatureThe reaction mixture was warmed to room temperature
2. washwashed with water (25 mL)
3. customThe organic layer was separated
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto provide a residue that
8. customwas purified by flash chromatography (12 g, Silica, 0-30% ethyl acetate in heptane)
9. customevaporated in vacuo

ORD record

ord-4f23083966d64f89a6a86960146b6e81

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08623889B2