Pyridine → 2-Chloro-4-fluoro-3-methylbenzonitrile

Participants

Reaction Steps

To a solution (50 ml) of 2-chloro-4-fluoro-3-methylbenzamide (4.69 g) and pyridine (2.97 g) in DMF was added dropwise oxalyl chloride (3.80 g) with stirring under ice-cooling at not more than 10° C. After stirring at the same temperature for 1 hr, the mixture was poured into ethyl acetate/water and partitioned. The organic layer was washed with water, aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the precipitated crystals were collected by filtration, washed with cold hexane and dried to give the title compound (3.00 g) as crystals.

Provenance & Evidence