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4,4′-二(4-氯甲酰苯氧基)二苯砜的合成

Synthesis of 4,4’-Bis(4-chloroformylphenoxy)diphenylsulfone

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【作者】 黄振钟霍毅罗秋燕刘卓盛寿日

【Author】 HUANG Zhen-Zhonga,HUO Yia,LUO Qiu-Yanb,LIU Zhuoa,SHENG Shou-Ria(aInstitutes of Chemistry and Chemical Engineering,Jiangxi Normal University,Nanchang 330027;bDepartment of Chemistry,Jinggangshan Teacher’s College,Ji’an)

【机构】 江西师范大学化学化工学院井冈山师范学院化学系江西师范大学化学化工学院 南昌330027南昌330027吉安

【摘要】 以DMF作溶剂,在四丁基氟化铵(TBAF)存在下,对甲基苯基三甲硅基醚(1)和4,4′-二氯二苯砜(2)于100℃反应1h,合成了4,4′-二(4-甲基苯氧基)二苯砜(3),产率为92%;加入催化量的N-溴代丁二酰亚胺(NBS)并在光照条件下,与氧气反应得到中间体-4,4′-二(4-羧基苯氧基)二苯砜(4),其产率达90%;将化合物4与二氯亚砜反应合成目标产物4,4′-二(4-氯甲酰基苯氧基)二苯砜(5),总收率为74.5%(以对甲基苯基三甲硅基醚为基准计算)。

【Abstract】 The reaction of p-methylphenyltrimethylsilyl ether(1) with 4,4’-dichlorodiphenylsulfone(2) in DMF and in the presence of tetrabutylammonium fluoride(TBAF) at 100 ℃ for 1 h afforded 4,4’-bis(4-methylphenoxy)diphenyl sulfone(3) in a yield of 92%.Then compopund 3 was oxidized in air to the corresponding intermediate 4,4’-bis(4-carboxyphenoxy)diphenyl sulfone(4) in a yield of 90% in the presence of a catalytic amount of N-bromosuccinimde(NBS) under photoirradiation.Subsequently the reaction of compound 4 with thionyl chloride yielded target compound 4,4’-bis(4-chloroformylphenoxy)diphenylsulfone(5) in a overall yield of about 74.5%(based on compound 1).The present method has the advantages of readily availability of starting materials,mild reaction conditions,convenient manipulation and good yields.

【基金】 国家自然科学基金(20664001);国家“八六三”计划(2002AA333120);江西省自然科学基金(0520028)资助项目
  • 【文献出处】 应用化学 ,Chinese Journal of Applied Chemistry , 编辑部邮箱 ,2007年08期
  • 【分类号】O625.7
  • 【被引频次】1
  • 【下载频次】267
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