甲基芳烃的侧链溴化新方法研究  

A New Method for α-Bromination of Methylarene

作　　者：申理滔[1] 陈红飙[1] 林原斌[1] 

机构地区：[1]湘潭大学化学学院环境友好化学与应用省部共建教育部重点实验室,湘潭411105

出　　处：《有机化学》2010年第2期272-275,共4页Chinese Journal of Organic Chemistry

基　　金：湖南省教育厅(No.03C461)资助项目

摘　　要：溴苄类化合物在医药、农药和染料等领域有广泛的应用,在以往的报道中由甲基芳烃制备溴苄类化合物的方法都是采用自由基的历程进行的.报道了一种以甲基芳烃与三溴化硼直接反应采用非自由基的历程制备系列溴甲基芳烃的新方法.该方法反应条件温和、收率高、选择性好.在考察电子效应和位阻效应时发现:该方法对不同取代基的底物适应范围广,带推电子取代基对反应有利;取代基位阻有一定影响但是没有吸电子基团显著,吸电子基团降低产率.同时,在研究溶剂、温度、三溴化硼用量和时间对反应的影响时找到了最佳反应条件.A new bromination of methylarenes was developed through boron tribromide under the mild conditions, which is different from traditional free-radical process. The advantage of this method is the good yield and high selectivity. During investigation of electron and steric effect, it was found that substrates with various substitutional groups could give expected products in moderate to good yields. Both steric hindrance and electron effect would affect the reaction. Electron-donating substitute was favorable to bromination, while electron-withdrawing group decreased the yield. At the same time, the influence of solvent, temperature, mass of boron tribromide and reaction time on the bromination was also investigated.

关 键 词：三溴化硼 溴化 甲基芳烃 溴甲基芳烃 

分 类 号：O621.2[理学—有机化学]