Sodium Hydroxide → 2'-acetyl-2-bromo-N-methylacetanilide

Participants

Reaction Steps

404 mg (2 mmol) of bromoacetyl bromide were added to a stirred, ice-cooled solution of 298 mg (2 mmol) of 2′-(methylamino)acetophenone in 5 ml of dichloromethane. The mixture was stirred for 20 minutes then 2 ml of 1M sodium hydroxide solution were added and stirring was continued for a further 15 minutes. The resulting solution was washed with 2M hydrochloric acid and saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated to dryness to give 2.1 g of 2′-acetyl-2-bromo-N-methylacetanilide as a viscous gum. 1H NMR (400 MHz CDCl3) δ: 2.54 (3H,s), 3.16 (3H,s), 3.45-3.52 (2H,q), 7.34 (1H,dd), 7.48 (1H,dt), 7.56 (1H,dt), 7.77 (1H,dd).

Provenance & Evidence