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.
利用 NBS、分子溴和光溴化法研究了 5-氨基茚满、5-乙酰氨基茚满和 5-乙酰氨基茚满-1-酮的溴化反应,并给出了最佳反应条件。在回流温度下,5-氨基茚满与冰乙酸反应生成 5-乙酰氨基茚满,收率高。5-acetamidoindane 与 CrO3 在乙酸中反应生成 5-乙酰氨基茚满-1-酮。在乙酸中用溴处理标题化合物,可在 5-乙酰氨基茚满的 C-6 位实现选择性溴化,从而得到 5-乙酰氨基-6-溴茚满。在不同的反应条件下,溴茚满酮还发生了进一步的溴化反应。