Hydrogen Bromide → 5-Chloroisoindoline hydrochloride

Participants

Reaction Steps

1.0 g of 2-(p-toluensulfonyl)-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 twice with 50 ml of ethyl acetate. The water layer was basified with aqueous sodium hydroxide solution and extracted with ethyl acetate three times. The extract was concentrated and the crude was diluted with 4N HCl/Dioxane and stirred for 15 minutes. Evaporate HCl, azeotrope with toluene three times to obtained 0.3 g of 5-Chloro-2,3-dihydro-1H-isoindole hydrochloride as a black solid. MS: [M+H]+ 153-15

Provenance & Evidence