Abstract
Readily available ethyl chlorofluoroacetate, when treated with a strong base, forms an alpha-chloro-alpha-fluorocarbanion that adds to nitroarenes at a position ortho or para to the nitro group with formation of anionic sigma(H) adducts. Subsequent base-induced beta-elimination of HCl proceeds selectively to give nitrobenzylic alpha-fluorocarbanions and, upon protonation, ethyl alpha-fluoro-alpha-nitroarylacetates.