Flow Photo-on-Demand Synthesis of Vilsmeier Reagent and Acyl Chlorides from Chloroform and Its Applications to Continuous Flow Synthesis of Carbonyl Compounds,Organic Process Research & Development

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Flow Photo-on-Demand Synthesis of Vilsmeier Reagent and Acyl Chlorides from Chloroform and Its Applications to Continuous Flow Synthesis of Carbonyl Compounds
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2023-09-15 , DOI: 10.1021/acs.oprd.3c00267
Yue Liu ₁ , Yukina Shirai ₁ , Itsuumi Okada ₁ , Ryota Ohmura ₁ , Fengying Liang ₁ , Akihiko Tsuda ₁

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Phosgene and the Vilsmeier reagent (VR), which are used in a wide variety of organic reactions, are unstable in air. Phosgene also has an extremely high toxicity. Their safe use, especially in industry, is an important issue in flow organic synthesis. The present study reports the flow synthesis of acyl chlorides and VR with phosgene (COCl₂) produced from the flow photochemical oxidation of chloroform (CHCl₃). This system is applicable to the continuous flow synthesis of esters, carboxylic anhydrides, amides, aryl aldehyde precursors, and β-chloroacrolein precursors. The confined space in the flow reaction system is preferable for safe and efficient conversion of (1) CHCl₃ to COCl₂ and (2) DMF to VR as well as (3) the subsequent chlorination of carboxylic acids, formylation of aromatic compounds, and chlorination and formylation of acetyl groups with VR.

中文翻译：

氯仿中Vilsmeier试剂和酰氯的流动光点播合成及其在羰基化合物连续流动合成中的应用

用于多种有机反应的光气和 Vilsmeier 试剂 (VR) 在空气中不稳定。光气还具有极高的毒性。它们的安全使用，特别是在工业中，是流动有机合成中的一个重要问题。本研究报道了氯仿（CHCl ₃ ）的流动光化学氧化产生的光气（COCl ₂ ）的流动合成酰氯和VR。该系统适用于酯类、羧酸酐类、酰胺类、芳醛前体、β-氯丙烯醛前体的连续流合成。流动反应系统中的有限空间有利于将 (1) CHCl ₃ 转化为 COCl ₂ 和 (2) DMF 转化为 VR 以及 (3)随后进行羧酸的氯化、芳香族化合物的甲酰化以及乙酰基与 VR 的氯化和甲酰化。

更新日期：2023-09-15

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