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A practical microwave method for the synthesis of fluoromethy 4-methylbenzenesulfonate in tert-amyl alcohol
Brocklesby, K.L. Waby, Jennifer S. Cawthorne, C. Smith, G.
Brocklesby, K.L.
Waby, Jennifer S.
Cawthorne, C.
Smith, G.
Publication Date
25/04/2018
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(c) 2018 The Authors. This is an Open Access article distributed under the Creative Commons CC-BY license (http://creativecommons.org/licenses/by/4.0/)
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15/03/2018
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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%).
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Brocklesby KL, Waby JS, Cawthorne C and Smith G (2018) A practical microwave method for the synthesis of fluoromethy 4-methylbenzenesulfonate in tert-amyl alcohol. Tetrahedron Letters. 59(17): 1635-1637.
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