Acetic Acid → 2-Chloro-6-(trifluoromethyl)pyridine-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6-(trifluoromethyl)nicotinonitrile (1.0 g, 4.84 mmol) was diluted with toluene (5.0 mL), placed under nitrogen and cooled to −78° C. DIBAL-H (9.68 mL, 9.68 mmol) was added dropwise and the reaction was stirred for 1 hour. The reaction was warmed to 0° C. and acetic acid (2 mL in 8 mL of water) was added dropwise. After stirring for 2 hours, the reaction was extracted twice with ethyl acetate, washed with Rochelle's salt, dried over MgSO4, filtered and concentrated. The material was loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 30% ethyl acetate/hexanes to yield 2-chloro-6-(trifluoromethyl)nicotinaldehyde (337 mg, 1.61 mmol, 33.2% yield) as a clear oil.

Provenance & Evidence