A Vilsmeier Chloroformylation by Continuous Flow Chemistry,Organic Process Research & Development

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A Vilsmeier Chloroformylation by Continuous Flow Chemistry
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2020-08-17 , DOI: 10.1021/acs.oprd.0c00318
Manuel Carrera ₁ , Laurens De Coen ₁ , Michelle Coppens ₂ , Wim Dermaut ₂ , Christian V. Stevens ₁

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Chloroformylation reactions are versatile reactions that allow the introduction of a chlorine atom and an aldehyde group in enolizable ketones, employing the well-known Vilsmeier reagent. However, the use of this unstable reagent is usually associated with hazards, especially when it is used on an industrial scale. The present article describes the preparation and use of the Vilsmeier reagent under continuous flow conditions for the preparation of an important intermediate in the synthesis of cyanine dyes. In addition, the traditionally used dimethylformamide has been substituted with more desirable formamides, together with the removal of the halogenated solvent usually employed in the reaction. Consequently, the optimized conditions allow the continuous production of the target compound in a 79–81% isolated yield in a more environmentally friendly, fast, and secure manner.

中文翻译：

连续流动化学进行的Vilsmeier氯甲酰化

氯甲酰化反应是通用的反应，它允许使用众所周知的Vilsmeier试剂在可烯醇化的酮中引入氯原子和醛基。但是，使用这种不稳定的试剂通常会带来危害，尤其是在工业规模上使用时。本文介绍了Vilsmeier试剂在连续流动条件下的制备和用途，用于制备合成花青染料的重要中间体。此外，传统上使用的二甲基甲酰胺已被更理想的甲酰胺取代，同时去除了反应中通常使用的卤代溶剂。所以，

更新日期：2020-10-17

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