(Trifluoromethyl)trimethylsilane → 1-(6-Bromopyridin-2-yl)-2,2,2-trifluoroethan-1-ol

Participants

Reaction Conditions

Reaction Steps

6-Bromopyridine-2-carbaldehyde (1.0 g, 5.38 mmol) was taken up in 35 mL THF and cooled to 0° C. TMSCF3 (1.0 mL, 6.45 mmol) was added followed by tetrabutylammonium fluoride (6.45 mL of 1.0M in THF). The reaction was stirred allowed to warm to room temperature and maintained at that temperature for 4.5 hours. The mixture was then diluted with water and brine, and extracted with ethyl acetate (3×). The organic layers were combined and dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography (0-40% ethyl acetate/hexanes) afforded the title compound.

Provenance & Evidence