{"title":"连续流合成(E)- o-（3-氯-2-丙烯基）羟胺：一种关键中间体","authors":"Chengxia Tan, Yang Chen, Junhui Wu, Mimi Li, Dang Cheng, Miaolin Ke, Fener Chen","doi":"10.1007/s41981-025-00348-1","DOIUrl":null,"url":null,"abstract":"<div><p>An efficient continuous flow process was developed for synthesizing (<i>E</i>)-O-(3-chloro-2-propenyl)hydroxylamine, a crucial intermediate of clethodim. This continuous flow manufacturing approach encompasses three chemical transformations from the simple and readily accessible material, hydroxylamine hydrochloride. Through a systematic series of screening tests conducted under various flow conditions, the traditional batch synthesis route was successfully simplified. The amide condensation reaction was achieved in just 70 s at room temperature within the flow system. Additionally, the chloroamination step was streamlined using a microreactor, significantly reducing the required reaction time and enhancing heat transfer efficiency. Finally, (<i>E</i>)-O-(3-chloro-2-propenyl)-hydroxylamine was furnished in 70% isolated yield with a purity of 96%, a total residence time of 18 min and 12.84 g/h throughput.</p><h3>Graphical Abstract</h3><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":630,"journal":{"name":"Journal of Flow Chemistry","volume":"15 2","pages":"79 - 88"},"PeriodicalIF":2.0000,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Continuous flow synthesis of (E)-O-(3-chloro-2-propenyl)hydroxylamine: a key intermediate of clethodim\",\"authors\":\"Chengxia Tan, Yang Chen, Junhui Wu, Mimi Li, Dang Cheng, Miaolin Ke, Fener Chen\",\"doi\":\"10.1007/s41981-025-00348-1\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>An efficient continuous flow process was developed for synthesizing (<i>E</i>)-O-(3-chloro-2-propenyl)hydroxylamine, a crucial intermediate of clethodim. This continuous flow manufacturing approach encompasses three chemical transformations from the simple and readily accessible material, hydroxylamine hydrochloride. Through a systematic series of screening tests conducted under various flow conditions, the traditional batch synthesis route was successfully simplified. The amide condensation reaction was achieved in just 70 s at room temperature within the flow system. Additionally, the chloroamination step was streamlined using a microreactor, significantly reducing the required reaction time and enhancing heat transfer efficiency. Finally, (<i>E</i>)-O-(3-chloro-2-propenyl)-hydroxylamine was furnished in 70% isolated yield with a purity of 96%, a total residence time of 18 min and 12.84 g/h throughput.</p><h3>Graphical Abstract</h3><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>\",\"PeriodicalId\":630,\"journal\":{\"name\":\"Journal of Flow Chemistry\",\"volume\":\"15 2\",\"pages\":\"79 - 88\"},\"PeriodicalIF\":2.0000,\"publicationDate\":\"2025-03-06\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Flow Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s41981-025-00348-1\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Flow Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s41981-025-00348-1","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Continuous flow synthesis of (E)-O-(3-chloro-2-propenyl)hydroxylamine: a key intermediate of clethodim
An efficient continuous flow process was developed for synthesizing (E)-O-(3-chloro-2-propenyl)hydroxylamine, a crucial intermediate of clethodim. This continuous flow manufacturing approach encompasses three chemical transformations from the simple and readily accessible material, hydroxylamine hydrochloride. Through a systematic series of screening tests conducted under various flow conditions, the traditional batch synthesis route was successfully simplified. The amide condensation reaction was achieved in just 70 s at room temperature within the flow system. Additionally, the chloroamination step was streamlined using a microreactor, significantly reducing the required reaction time and enhancing heat transfer efficiency. Finally, (E)-O-(3-chloro-2-propenyl)-hydroxylamine was furnished in 70% isolated yield with a purity of 96%, a total residence time of 18 min and 12.84 g/h throughput.
期刊介绍：
The main focus of the journal is flow chemistry in inorganic, organic, analytical and process chemistry in the academic research as well as in applied research and development in the pharmaceutical, agrochemical, fine-chemical, petro- chemical, fragrance industry.
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