Continuous Flow Production of Thermally Unstable Intermediates in a Microreactor with Inline IR-Analysis: Controlled Vilsmeier–Haack Formylation of Electron-Rich Arenes

The Vilsmeier–Haack formylation of aromatic compounds is a well-established process in organic synthesis, largely driven by the fact that the resulting aldehydes are generally useful intermediates for the synthesis of fine chemicals and pharmaceutical products. Industrial-scale production, however,...

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Published inOrganic process research & development Vol. 16; no. 5; pp. 934 - 938
Main Authors van den Broek, Sebastiaan (Bas) A. M. W, Leliveld, Jeroen R, Becker, René, Delville, Mariëlle M. E, Nieuwland, Pieter J, Koch, Kaspar, Rutjes, Floris P. J. T
Format Journal Article
LanguageEnglish
Published American Chemical Society 18.05.2012
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Summary:The Vilsmeier–Haack formylation of aromatic compounds is a well-established process in organic synthesis, largely driven by the fact that the resulting aldehydes are generally useful intermediates for the synthesis of fine chemicals and pharmaceutical products. Industrial-scale production, however, is often hampered by laborious procedures requiring the use of hazardous chemicals to produce the highly reactive intermediates. In order to circumvent these issues, a flow chemistry approach was developed. This article describes the design and semiautomated optimization of the Vilsmeier–Haack formylation in continuous flow and subsequent scale-up to preparative volumes in an intrinsically safe manner.
ISSN:1083-6160
1520-586X
DOI:10.1021/op2003437