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<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&#xa0;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&#xa0;min and 12.84&#xa0;g/h throughput.</p> Graphical Abstract <p></p>

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Continuous flow synthesis of (E)-O-(3-chloro-2-propenyl)hydroxylamine: a key intermediate of clethodim

  • 期刊论文

  • 发表日期：

    2025年3月6日

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  • Chengxia Tan,
  • Yang Chen,
  • Junhui Wu,
  • Mimi Li,
  • Dang Cheng,
  • Miaolin Ke,
  • Fener Chen

摘要

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.

Graphical Abstract