Pyridine → N-(2-Bromo-4,6-difluorophenyl)-2,2-dimethylpropanamide

Participants

Reaction Steps

2-Bromo-4,6-difluoroaniline (10.4 g, Aldrich) was dissolved in dichloromethane (75 ml) and treated with pyridine (4.63 g) in an ice bath. 4-Dimethylaminopyridine (0.61 g) was then added and the mixture was allowed to warn to room temperature. After dropwise addition of pivaloyl chloride (7.23 g, BDH), the reaction was stirred for 5 hours. On completion, the mixture was added to diethyl ether (250 ml), washed twice with 2M HCI (250 ml) and the resulting organic layer was treated with saturated NaHCO3 (2×250 ml). The organic layer was washed with water (250 ml), and dried over MgSO4. Removal of the solvent from the filtrate gave the crude title product as a white solid (13.40 g).

Provenance & Evidence