Boron tribromide → 6-hydroxy-2,3-dihydro-1H-indol-2-one

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Reaction Steps

The solution of 3.26 of 6-methoxy-2-oxindole in 60 mL of dischloromethane was cooled at −3° C. and 10 mL of 1 M boron tribromide solution in dichloromethane was added dropwise. The reaction mixture was stirred in ice-bath for 1 hour, room temperature for 1 hour, poured into ice water, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, concentrated, and dried in a vacuum oven overnight to give 2.56 g of the 6-hydroxy-2-oxindole (86% yield),

Provenance & Evidence