Hydrogen Bromide → N-[2-(2-bromoacetyl)phenyl]acetamide

Participants

Reaction Steps

31 g (0.175 mol) of N-(2-acetylphenyl)acetamide (prepared by acylating 2-aminoacetophenone with acetyl chloride according to Fuerstner, Alois; Jumbam, Denis N.; Tetrahedron; 48; 29; 5991-6010, (1992)) were dissolved in 200 ml of glacial acetic acid. 127 ml of 33% HBr in glacial acetic acid were added and then 8.75 ml (0.175 mol) of bromine were added slowly at room temperature. The mixture was stirred at room temperature overnight. The mixture was stirred into 1.5 l of ice-water, and the precipitated product was filtered off with suction, washed thoroughly with ice-water and dried in vacuo. According to HPLC and NMR, the crude product contained some reactant and dibrominated product, but was clean enough for the further reaction (approx. 85%).

Provenance & Evidence