N-(4-bromophenyl)propanamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-bromoaniline (9.0 g, 52.3 mmol) in PhMe (100 mL) and pyridine (8.5 mL, 110 mmol, 2.0 eq.) was cooled in an ice bath and slowly treated with propionyl chloride (5.5 mL, 63 mmol, 1.2 eq.). After 2 h, the reaction mixture was added to 0.1 M HCl and extracted into EtOAc. Concentration followed by recrystallization of the residue from EtOH/water gave N-propionyl-4-bromoaniline (10.64 g, 89%). [M−H]−=278.1 m/z. extracted into EtOAc Concentration followed by recrystallization of the residue from EtOH/water