Ammonia → 2,5-Dichloro-4-(trifluoromethyl)pyridine

Participants

Reaction Steps

Copper iodide (1.67 g) and potassium fluoride (0.51 g) were subjected to a reduced pressure (1 Torr) using a vacuum pump, and were heated with a heat gun for 20 minutes while stirring slowly. Under the argon atmosphere, 14 ml of N-methylpyrrolidine and 1.25 g of trifluoromethyltrimethylsilane were added, and a temperature was elevated to 50° C. over 20 minutes. After further stirring for 30 minutes, 2 g of 2,5-dichloro-4-iodopyridine was added, and the mixture was stirred for 20 hours. After allowing to cool, the reaction solution was poured into a 12% aqueous ammonia solution, the resultant solution was extracted with diethyl ether three times, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 1 g of 2,5-dichloro-4-trifluoromethylpyridine.

Provenance & Evidence