Continuous-Flow Diazotization for Efficient Synthesis of Methyl 2-(Chlorosulfonyl)benzoate: An Example of Inhibiting Parallel Side Reactions

被引：19
|
作者：
Yu, Zhiqun [1 ]
Dong, Hei [1 ]
Xie, Xiaoxuan [1 ]
Liu, Jiming [2 ]
Su, Weike [1 ,2 ]
机构：
[1] Zhejiang Univ Technol, Natl Engn Res Ctr Proc Dev Act Pharmaceut Ingredi, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Minist Educ, Key Lab Green Pharmaceut Technol & Related Equipm, Hangzhou 310014, Zhejiang, Peoples R China
来源：
ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2016年 / 20卷 / 12期
基金：
中国国家自然科学基金;
关键词：
diazotization; continuous flow; parallel side reaction; chlorosulfonylation; CHEMISTRY; REACTORS; DESIGN; TECHNOLOGY; GENERATION; REAGENTS;
D O I：
10.1021/acs.oprd.6b00238
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An expeditious process for the highly efficient synthesis of methyl 2-(chlorosulfonyl)benzoate was described, which involved the continuous-flow diazotization of methyl 2-aminobenzoate in a three-inlet flow reactor via a cross joint followed by chlorosulfonylation in the tandem tank reactor. The side reaction such as hydrolysis was decreased eminently from this continuous-flow process even at a high concentration of hydrochloric acid. The mass flow rate of methyl 2-aminobenzoate was 4.58 kg/h, corresponding to an 18.45 kg/h throughput of diazonium salt solution. The potential of inhibiting parallel side reactions by conducting in a flow reactor was successfully demonstrated in this method.
引用
收藏
页码：2116 / 2123
页数：8
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