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Published on: January 19, 2016
A General Method for Nucleophilic Aromatic Substitution of Aryl Fluorides and Chlorides with Dimethylamine using
Juana Garcia1, Jacob Sorrentino1, Emily J Diller1
1Department of Physical and Life Sciences, Nevada State College, Henderson, NV 89002.
Abstract:
A practical and convenient procedure for the nucleophilic aromatic substitution of aryl fluorides and chlorides with dimethylamine was developed using a hydroxide assisted, thermal decomposition of N,N-dimethylforamide. These conditions are tolerant of nitro, nitrile, aldehyde, ketone, and amide groups but will undergo acyl substitution to form amides for methyl esters and acyl chlorides. Isolated yields of the products range from 44 - 98%, with the majority being greater than 70% for seventeen examples.
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