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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (11): 1742-1744. 上一篇    下一篇

研究简报

二-(4-溴-2,5-二烷氧基苯基)甲烷及其类似物的合成

陈志钊，曹德榕*   

  1. (华南理工大学化学与化工学院 广州 510640)
  • 收稿日期:2010-03-31 修回日期:2010-06-05 发布日期:2010-06-11
  • 通讯作者: 曹德榕 E-mail:drcao@scut.edu.cn
  • 基金资助:

    国家自然科学基金

Synthesis of Bis(4-bromo-2,5-dialkoxyphenyl)methane and Its Ana-logues

CHEN Zhi-Zhao, CAO De-Rong   

  1. (School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640)
  • Received:2010-03-31 Revised:2010-06-05 Published:2010-06-11
  • Contact: Derong Cao E-mail:drcao@scut.edu.cn

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被引次数

5

报道二-(4-溴-2,5-二烷氧基苯基)甲烷的一种简便合成方法. 1,4-二乙氧基-2,5-二(烷氧基甲基)苯(1)在对甲苯磺酸催化下生成柱形杯[5]芳烃化合物2|2与N-溴代丁二酰亚胺(NBS)反应, 生成二-(4-溴-2,5-二烷氧基苯基)甲烷(3). 该方法反应条件温和、操作简单、选择性好、收率高. 2与硝酸发生硝化反应, 生成二-(4-硝基-2,5-二甲氧基苯基)甲烷(4). 所合成的二-(4-溴-2,5-二烷氧基苯基)甲烷和二-(4-硝基-2,5-二甲氧基苯基)甲烷经过1H NMR, 13C NMR和MS表征确认.

关键词: 柱形杯芳烃, N-溴代丁二酰亚胺, 溴代, 二苯甲烷

A novel synthetic method for preparation of bis(4-bromo-2,5-dialkoxyphenyl)methane and bis(4-nitro-2,5-dimethoxyphenyl)methane was reported. 1,4-Bis(ethoxymethyl)-2,5-dialkoxybenzene (1) was treated in boiling dichloromethane with catalytic amounts of p-toluenesulfonic acid gave pillar[5]arenes 2. 2 reacted with N-bromosuccinimide (NBS) in acetone under refluxing gave bis(4-bromo-2,5-dimethoxy- phenyl)methane (3). Nitration of 2 with nitric acid gave bis(4-nitro-2,5-dimethoxyphenyl)methane (4). This synthetic method has some advantages, such as mild reaction conditions, simple operation, high selectivity and good yield. The structures of 3 and 4 were confirmed by 1H NMR, 13C NMR and MS techniques.

Key words: pillararene, N-bromosuccinimide, bromination, diphenylmethane