Hydrochloric Acid → HCID 53416101, compound

Participants

Reaction Steps

Lithium chloride (0.500 g, 11.79 mmol) and diisopropylamine (1.8 mL, 12.84 mmol) were combined under nitrogen with dry tetrahydrofuran (10 mL) and cooled in a dry ice bath. N-Butyllithium (2.5 M solution in hexane, 5.0 mL, 12.50 mmol) was added and the mixture stirred for 10 minutes. 2-Fluoropyridine (0.800 mL, 9.30 mmol) was added dropwise and the reaction stirred. After 10 minutes, additional dry tetrahydrofuran (5 mL) was added to help with stirring. The mixture was stirred for 90 minutes then ethyl trifluoroacetate (1.7 mL, 14.30 mmol) was added dropwise. After 60 minutes the reaction was quenched by addition of hydrochloric acid (5N in 2-propanol, 5 mL, 10 mmol). The mixture was warmed to room temperature and water (150 mL) and ethyl acetate (200 ml) were added. The phases were mixed and separated and the organic dried with magnesium sulfate. Purification using silica chromatography (hexane to ethyl acetate gradient) gave the desired 2,2,2-trifluoro-1-(2-fluoropyridin-3-yl)ethanone (0.812 g, 4.21 mmol, 45.2% yield).

Provenance & Evidence