Sodium Carbonate → 5-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

Participants

Reaction Steps

A solution of bromine (1.98 g) in acetic acid (10 cm3) was added dropwise to a stirred solution of 3,3-dimethyl-indol-2-one (2.0 g) and sodium acetate (1.01 g) in acetic acid (10 cm3). The mixture was stirred at room temperature for 30 minutes, poured onto water (20 cm3), basified to pH9 with sodium carbonate, and extracted with ethyl acetate (3×50 cm3). The combined and dried (MgSO4) organic extracts were evaporated in vacuo and the residue chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with methanol:hexane:dichloromethane, 1:10:40 by volume. Combination and evaporation of the appropriate fractions gave the title compound, m.p. 166°-166.5° (2.15 g).

Provenance & Evidence