N-Ethylaniline → N-ethyl-2-bromo-5-nitro-N-phenyl-benzamide

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (1.65 ml, 2.3 g, 18.3 mmol) was added dropwise to a solution of 2-bromo-5-nitrobenzoic acid (3 g, 12.2 mmol) in dichloromethane (12 ml). N,N-Dimethylformamide (0.01 ml) was added to the reaction mixture via syringe, the reaction mixture was stirred at 23° C. for 4 hour. The reaction mixture was concentrated in vacuo, and the residue was taken up in dichloromethane (24 ml), and DMAP (10 mg) and triethylamine (3.4 ml, 2.5 g, 24.3 mmol) were added. N-Ethylaniline (1.8 ml, 1.8 g, 14.6 mmol) was added over a 10 min period. After 18 hours at this temperature, 1:1 ethyl acetate/hexanes (30 ml) was added, and the organics were washed with 1N HCl (2-30 ml portions) and saturated aqueous sodium chloride (30 mL). The organics were dried over anhydrous sodium sulfate and concentrated. Purification of the residue by recrystallization from ethyl acetate/hexanes afforded N-ethyl-2-bromo-5-nitro-N-phenyl-benzamide (3.8 g, 60%).

Provenance & Evidence