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.

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%).

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

• Journal Article Type: Article
• Acceptance Date: Mar 15, 2018
• Online Publication Date: Mar 16, 2018
• Publication Date: Apr 25, 2018
• Deposit Date: Apr 9, 2019
• Publicly Available Date: Apr 10, 2019
• Journal: Tetrahedron Letters
• Print ISSN: 0040-4039
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 59
• Issue: 17
• Pages: 1635-1637
• DOI: https://doi.org/10.1016/j.tetlet.2018.03.039
• Keywords: PET; Fluorination; Microwave; Fluoromethyl tosylate; Tert-amyl alcohol
• Public URL: https://hull-repository.worktribe.com/output/1563191
• Publisher URL: https://www.sciencedirect.com/science/article/pii/S0040403918303538?via%3Dihub
• Contract Date: Apr 9, 2019