7-溴-1-茚满酮的合成研究

Synthesis of 7-Bromo-1-indanone

研究了标题化合物的新合成方法。以邻溴苯乙酮为原料,经α-亚甲基化、亲电加成以及分子内傅克烷基化反应合成了目标产物。研究发现,影响总收率的关键步骤是邻溴苯乙酮的α-亚甲基化反应。探讨了反应溶剂、反应温度、反应时间及铵盐类型等条件对邻溴苯乙酮α-亚甲基化反应的影响。结果发现,在以四氢呋喃为溶剂和使用二乙胺三氟乙酸盐的条件下,可近定量得到邻溴苯乙酮α-亚甲基化产物。所有产物经NMR和MS进行确证。

A new method for the synthesis of 7-bromo-1-indanone was developed by α-methylation of 2-bromoacetophenone,electrophilic addition with hydrochloride and subsequent intramolecular Friedel-Crafts alkylation.It was found that the key step is theα-methylenation of the o-bromoacephenone.The effects of solvents,temperature,reaction time and ammonium salts on the yield ofα-methylation of 2-bromoacetophenone were investigated.It is found that the product of α-methylation could be obtained near quantatively in tetrahydrofuran using diethylammoniumtrifluoroacetate.All products were confirmed by NMR and MS.