Water → 3-Acetyl-2-chloropyridine

Participants

Reaction Steps

A mixture of 2-chloronicotinic acid chloride (8.8 g, 49.5 mmol), tetramethyltin (5.5 mL, 40 mmol) and bis(benzonitrile)palladium(II) chloride (0.385 g) in 20 mL of hexamethylphosphoramide was stirred at room temperature for 20 hours. The mixture was stirred with 50 mL of 10% potassium fluoride and then poured into 50 mL of water. The mixture was extracted with diethyl ether (4×50 mL) and the combined extracts were washed with water, saturated sodium bicarbonate and sodium chloride, dried (Na2SO4) and concentrated. The residue was purified on silica gel by column chromatography eluting with hexanes/ethyl acetate (3:1) to give 3-acetyl-2-chloropyridine (4.2 g, 27 mmol).

Provenance & Evidence