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A practical microwave method for the synthesis of fluoromethy 4-methylbenzenesulfonate in tert-amyl alcohol

Brocklesby, Kayleigh L.; Waby, Jennifer S.; Cawthorne, Christopher; Smith, Graham D.

Authors

Kayleigh L. Brocklesby

Jennifer S. Waby

Christopher Cawthorne

Graham D. Smith



Abstract

Fluorine substitution is an established tool in medicinal chemistry to favourably alter the molecular properties of a lead compound of interest. However, gaps still exist in the library of synthetic methods for accessing certain fluorine-substituted motifs. One such area is the fluoromethyl group, particularly when required in a fluoroalkylating capacity. The cold fluorination of methylene ditosylate is under evaluated in the literature, often proceeding with low yields or harsh conditions. This report describes a novel microwave method for the rapid nucleophilic fluorination of methylene ditosylate using inexpensive reagents in good isolated yield (65%).

Journal Article Type Article
Publication Date Apr 25, 2018
Journal Tetrahedron Letters
Print ISSN 0040-4039
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 59
Issue 17
Pages 1635-1637
APA6 Citation Brocklesby, K. L., Waby, J. S., Cawthorne, C., & Smith, G. D. (2018). A practical microwave method for the synthesis of fluoromethy 4-methylbenzenesulfonate in tert-amyl alcohol. Tetrahedron letters; the international organ for the rapid publication of preliminary communications in organic chemistry, 59(17), 1635-1637. https://doi.org/10.1016/j.tetlet.2018.03.039
DOI https://doi.org/10.1016/j.tetlet.2018.03.039
Keywords PET; Fluorination; Microwave; Fluoromethyl tosylate; Tert-amyl alcohol
Publisher URL https://www.sciencedirect.com/science/article/pii/S0040403918303538?via%3Dihub

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Copyright Statement
©2018 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/.)





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