Pivaloyl chloride → N-(4-bromo-2-fluorophenyl)-2,2-dimethylpropanamide

Participants

Reaction Steps

Pivaloyl chloride (72 mL, 580 mmol) was added slowly (caution—exothermic reaction) to an ice cold solution of 4-bromo-2-fluoroaniline (100 g, 526 mmol) in pyridine (200 mL). After the addition, the ice bath was removed and the hot reaction mixture was stirred at room temperature for 30 minutes. The mixture was poured into cold water (500 mL) and the precipitated product was collected by filtration and washed with 1N HCl. The solid was dissolved in EtOAc (1 L), dried over MgSO4, filtered, and concentrated under vacuum to provide N-(4-bromo-2-fluorophenyl)-2,2-dimethylpropanamide (125 g).

Provenance & Evidence