P-Toluenesulfonamide → 5-Bromo-2-(p-tolylsulfonyl)isoindoline

Participants

Reaction Conditions

Reaction Steps

In 70 ml of N,N-dimethylformamide was suspended 3.97 g of sodium hydride (purity: 60%), followed by adding thereto 50 ml of a N,N-dimethylformamide solution containing 8.49 g of p-toluenesulfonamide, and the resulting mixture was stirred at 60° C. for 30 minutes. A solution of 17.0 g of 1-bromo-3,4-di(bromomethyl)benzene in 50 ml of N,N-dimethylformamide was added to the reaction mixture at 60° C. and the resulting mixture was stirred at the same temperature for 1 hour. The reaction mixture obtained was added to 500 ml of ice water and the precipitate was collected by filtration and purified by a column chromatography (eluent: chloroform) to obtain 15.2 g of 5-bromo-2-(p-toluenesulfonyl)isoindoline as colorless crystals.

Provenance & Evidence