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

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%).

SUBMITTER: Brocklesby KL

PROVIDER: S-EPMC5896226 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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A practical microwave method for the synthesis of fluoromethy 4-methylbenzenesulfonate in <i>tert</i>-amyl alcohol.

Brocklesby Kayleigh L KL Waby Jennifer S JS Cawthorne Christopher C Smith Graham G

Tetrahedron letters 20180401 17

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 ...[more]

PMID: 29706675

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