1-(2,3-Dihydro-1H-indol-1-yl)ethan-1-one → 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-bromoethanone

Participants

Reaction Steps

Bromoacetyl bromide (1.0 mL, 11.2 mmol) was slowly added to a suspension of aluminum chloride (3.7 g, 27.9 mmol) in dichloromethane (30 mL) and the reaction mixture was stirred for 20 min at rt. A solution of 1-acetylindoline (1.5 g, 9.3 mmol) in dichloromethane (10 mL) was slowly added and then the reaction mixture was heated at 55° C. for 1.5 h. The mixture was cooled and then quenched with cold water. The precipitate was filtered through a short pad of celite, washed with dichloromethane and water. The aqueous phase was extracted with dichloromethane. The combined organic extract was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to to give the product. Yield: 1.9 g (73%).

Provenance & Evidence