Azobisisobutyronitrile → 6-Bromomethyl-1-(3-methoxypropyl)-3,3-dimethyl-1,3-dihydroindol-2-one

Participants

Reaction Steps

The mixture of 1.08 g of 1-(3-methoxypropyl)-3,3,6-trimethyl-1,3-dihydroindol-2-one, 0.801 g of N-bromosuccinimide, 0.014 g of 2,2′-azobis(2-methylpropionitrile) and 0.021 g of dibenzoyl peroxide in 50 ml of carbon tetrachloride is heated to reflux with stirring. The reaction mixture is stirred at reflux over 1 hour (succinimide crystallizes out) and subsequently cooled to room temperature. The succinimide is filtered off and the filtrate is concentrated by evaporation. The title compound is obtained as a slightly orange oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.40 (dichloromethane-diethyl ether); Rt=17.22 (II).

Provenance & Evidence