2-(4-溴-2-(氯磺酰基)苯氧基)乙酸乙酯的合成研究  

Synthesis of Ethyl 2-(4-Bromo-2-(chlorosulfonyl)phenoxy)Acetate

作　　者：张茂风 王昌铭 郭秋玉 吴锡山 ZHANG Mao-feng;WANG Chang-ming;GUO Qiuyu;WU Xi-shan(College of Pharmacy,Taizhou Polytechnic College,Taizhou 225300,China;Jiangsu Solid Preparation Engineering Technology Research and Development Center,Taizhou 225300,China)

机构地区：[1]泰州职业技术学院药学院,江苏泰州225300 [2]江苏省固体制剂工程技术研究开发中心,江苏泰州225300

出　　处：《化学试剂》2020年第4期468-471,共4页Chemical Reagents

基　　金：江苏省自然科学基金资助项目(BK20190246);江苏省高校自然科学研究项目(19KJB350011);泰州职业技术学院院级科研项目(TZYKY-18-30)。

摘　　要：标题化合物是一种含有多官能团的磺酰氯衍生物,在构建新型活性先导化合物方面具有重要作用。该化合物及其合成方法目前尚无文献报道。以对溴苯酚为原料,经取代、氯磺化首次实现了目标化合物的合成。此外,提供了氯磺化步骤中可能的反应机理,为一锅法的建立提供理论依据。通过对投料比、反应物浓度、反应时间和反应温度等因素进行考察,确定较佳的工艺条件为n(2-(4-溴苯氧基)乙酸乙酯)∶n(氯磺酸)∶n(氯化亚砜)=1∶6∶13、反应时间为4.5 h、反应温度为室温。目标产物经1HNMR、13CNMR、MS和IR确证。该合成路线步骤短、操作简单,总收率达82%,适合工业化生产。The title compound is a sulfonyl chloride derivative with multifunctional groups which is important for the construction of novel active lead compounds.At present,the compound and its synthetic methods have not been reported in the literature.The target compound was synthesized by substitution and chlorosulfonation of the raw material of p-bromophenol.In addition,this work presents a presumed reaction mechanism of the chlorosulfonation step,which provides a theoretical basis for the establishment of one-plot synthetic method.The effects of feeding ratio,concentration of reactants,reaction time and reaction temperature were investigated.The preferred conditions were obtained as follows:the material ratio of n(ethyl 2-(4-bromophenoxy)acetate))∶n(chlorosulfonic acid)∶n(thionyl chloride)was 1∶6∶13,under the reaction time of 4.5 h,and the reaction temperature of room temperature.The structure of target compound was confirmed by 1HNMR,13CNMR,MS and IR.The synthetic route has the advantages of short steps,simple procedure for operation and an overall yield of 82%,which is suitable for industrial production.

关 键 词：2-(4-溴-2-(氯磺酰基)苯氧基)乙酸乙酯 对溴苯酚 磺酰氯 氯磺化反应 一锅法 合成 

分 类 号：O625.75[理学—有机化学]