二-(4-溴-2,5-二烷氧基苯基)甲烷及其类似物的合成

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

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.

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.