Hydrogen Bromide → 5-Chloroisoindoline

Participants

Reaction Steps

1.0 g of 2-(p-toluenesulfonyl)-5-chloroisoindoline and 1.0 g of phenol were added to a mixture of 8 ml of 48% hydrobromic acid and 1.4 ml of propionic acid, and the mixture was refluxed for 6 hours. The resultant reaction mixture was diluted with 10 ml of water and extracted 2 times with 50 ml of ether. The water layer was basified with aqueous sodium hydroxide solution and extracted with 50 ml of ether 4 times. The extract was concentrated and the residue was purified by vacuum distillation (bath temperature: 130°-140 ° C., pressure: 7 mmHg) to obtain 256 mg of 5-chloroisoindoline.

Provenance & Evidence