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有机化学
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有机化学 ›› 2012, Vol. 32 ›› Issue (01): 174-177.DOI: 10.6023/cjoc1106221 上一篇    下一篇

研究简报

3,5-二烷氧基甲苯的溴化反应研究

顾烨, 石洪卫, 陈丽媛, 沈永嘉   

  1. 华东理工大学精细化工研究所 结构可控先进功能材料及其制备教育部重点实验室 上海 200237
  • 收稿日期:2011-06-22 修回日期:2011-08-24 发布日期:2011-09-19
  • 通讯作者: 沈永嘉 E-mail:yjshen@ecust.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21076078)资助项目.

Bromination of 3,5-Dialkyloxytoluene

Gu Ye, Shi Hongwei, Chen Liyuan, Shen Yongjia   

  1. Laboratory for Advanced Materials, Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237
  • Received:2011-06-22 Revised:2011-08-24 Published:2011-09-19
  • Contact: Yong-Jia SHEN E-mail:yjshen@ecust.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21076078).

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3,5-二甲氧基甲苯在偶氮二异丁腈的存在下与N-溴代丁二酰亚胺(NBS)反应, 产物不是3,5-二甲氧基苄溴, 而是2-溴-3,5-二甲氧基甲苯和2,6-二溴-3,5-二甲氧基甲苯. 同样条件下, 3,5-二乙酰氧基甲苯与NBS 反应则生成3,5-二乙酰氧基苄溴. GAUSSIAN 03 计算的结果表明, 3,5-二甲氧基甲苯中苯环碳原子上的电荷密度高于侧链上碳原子上的电荷密度, 因此溴自由基更容易取代苯环上的氢, 而3,5-二乙酰氧基甲苯的情况恰好相反, 故产物是3,5-二乙酰氧基苄溴.

关键词: 3,5-二甲氧基甲苯, 3,5-二乙酰氧基甲苯, N-溴代丁二酰亚胺, 3,5-二乙酰氧基苄溴

When 3,5-dimethoxy-toluene reacted with N-bromosuccinimide (NBS) in the presence of azobisisobutyronitrile, the product was not 3,5-dimethoxy benzylbromide, but a mixture of 2-bromo-3,5-dimethoxy-toluene and 2,6-dibromo-3,5- dimethoxy-toluene. Under the same conditions, 3,5-diacetoxy-toluene reacted with NBS to generate 3,5-diacetoxy-benzyl bromide. The charge density distributions calculated by GAUSSIAN 03 indicated that the charge density of carbon atom of benzene ring in 3,5-dimethoxy-toluene was higher than the one of the carbon atom of the side chain. Thus, bromine radical was easy to replace the hydrogen in the ring. While the charge density distributions of 3,5-diacetoxy toluene was quite the opposite, hence, the product was 3,5-diacetoxy-benzyl bromide.

Key words: 3,5-dimethoxy-toluene, 3,5-diacetoxy-toluene, N-bromosuccinimide, 3,5-diacetoxy-benzyl bromide