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%).
Highlights
The use of fluorine in medicinal chemistry and agrochemicals has grown rapidly in recent years, culminating in approximately one third of the top selling drugs in the world containing at least one fluorine atom.[1]
A further avenue of interest for fluorine is nuclear medicine, Positron Emission Tomography (PET), where incorporation of cyclotron-produced fluorine-18 into radiopharmaceuticals is of widespread interest.[4]
Fluoromethylation is an underexplored strategy in both medicinal chemistry and nuclear medicine, partly as a result of the complex synthetic methodology required to access the necessary structures
Summary
A practical microwave method for the synthesis of fluoromethy 4-methylbenzenesulfonate in tert-amyl alcohol. Article history: Received 14 January 2018 Revised 12 March 2018 Accepted March 2018 Available online March 2018. Gaps still exist in the library of synthetic methods for accessing certain fluorine-substituted motifs. One such area is the fluoromethyl group, 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%).
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
