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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (02): 272-275. 上一篇    下一篇

研究简报

甲基芳烃的侧链溴化新方法研究

申理滔，陈红飙，林原斌*   

  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)
  • 收稿日期:2009-04-08 修回日期:2009-08-24 发布日期:2010-02-20
  • 通讯作者: 林原斌 E-mail:lyb@xtu.edu.cn
  • 基金资助:

    国家级.国家自然科学基金

A New Method for α-Bromination of Methylarene

Shen Litao Chen Hongbiao Lin Yuanbin*   

  1. (Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, Department of Chemistry, Xiangtan University, Xiangtan 411105)
  • Received:2009-04-08 Revised:2009-08-24 Published:2010-02-20

PDF

2370

被引次数

11 | 3

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.

关键词: 三溴化硼, 溴化, 甲基芳烃, 溴甲基芳烃

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.

Key words: boron tribromide, bromination, methylarene, bromomethylarene