Issue 10, 2005

Elemental fluorine

Part 18. Selective direct fluorination of 1,3-ketoesters and 1,3-diketones using gas/liquid microreactor technology

Abstract

1,3-Ketoesters and 1,3-diketones react with fluorine gas, using Durham multichannel modular microreactor technology, on a preparatively useful scale. High conversions and yields of monofluorinated products were obtained. A consideration of the mechanism of fluorination of dicarbonyl systems provides a rationale of the scope and limitations of the use of microreactor technology for such direct fluorination processes. We conclude that it is especially appropriate for the fluorination of diketones and ketoesters that exist mainly in the enol form at equilibrium and/or undergo rapid keto–enol interconversion. A one-stage route to fluoroketones from ketoesters was achieved by allowing the crude product mixture obtained from the fluorination of the ketoesters to stand for a period of time before reaction work-up.

Graphical abstract: Elemental fluorine Part 18. Selective direct fluorination of 1,3-ketoesters and 1,3-diketones using gas/liquid microreactor technology

Supplementary files

Article information

Article type
Paper
Submitted
04 Apr 2005
Accepted
27 Jun 2005
First published
15 Aug 2005

Lab Chip, 2005,5, 1132-1139

Elemental fluorine

R. D. Chambers, M. A. Fox and G. Sandford, Lab Chip, 2005, 5, 1132 DOI: 10.1039/B504675K

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