Synthesis of bromoaminoindane and bromoaminoindanone derivatives

Abstract

The bromination reactions of 5-aminoindane, 5-acetamidoindane, and 5-acetamidoindan-1-one were investigated using NBS, molecular bromine and photobromination, and the optimum reaction conditions were presented. The reaction of 5-aminoindane with glacial acetic acid at reflux temperature resulted in the formation of 5-acetamidoindane in high yield. 5-Acetamidoindan-1-one was generated by the reaction of 5-acetamidoindane with CrO3 in acetic acid. Selective bromination at C-6 position of 5-acetamidoindane was achieved by treatment of title compound with bromine in acetic acid and thus afforded 5-acetamido-6-bromoindane. Further bromination reactions of bromoindanones were achieved in various reaction conditions.