Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (01): 174-177.DOI: 10.6023/cjoc1106221 Previous Articles     Next Articles



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
  • 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
  • Supported by:

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

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