Chlorosuccinimide → 6'-Bromo-5'-chlorospiro[cyclopentane-1,3'-indolin]-2'-one

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Reaction Steps

N-Chlorosuccinimide (500 mg, 3.75 mmol) was added to a solution of 6′-bromospiro[cyclopentane-1,3′-indolin]-2′-one (preparation 2, 0.20 g, 0.75 mmol) in chloroform (5 mL). The mixture was stirred and heated to reflux. After 6 hours, the mixture was cooled to room temperature. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction and the mixture was extracted with chloroform. The organic layer was washed with brine, dried (MgSO4) and evaporated. Purification of the residue by flash chromatography (8:2 hexanes/ethyl acetate) gave the title compound (0.17 g, 75%) as a white solid.

Provenance & Evidence