Synthesis of α‑Fluoro-α-nitroarylacetates via Vicarious Nucleophilic Substitution of Hydrogen

Readily available ethyl chlorofluoroacetate, when treated with a strong base, forms an α-chloro-α-fluorocarbanion that adds to nitroarenes at a position ortho or para to the nitro group with formation of anionic σH adducts. Subsequent base-induced β-elimination of HCl proceeds selectively to give ni...

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Veröffentlicht in:	Journal of organic chemistry 2016-12, Vol.81 (23), p.11751-11757
Hauptverfasser:	Czaban-Jóźwiak, Justyna, Loska, Rafał, Mąkosza, Mieczysław
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Sprache:	eng
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creator	Czaban-Jóźwiak, Justyna Loska, Rafał Mąkosza, Mieczysław
description	Readily available ethyl chlorofluoroacetate, when treated with a strong base, forms an α-chloro-α-fluorocarbanion that adds to nitroarenes at a position ortho or para to the nitro group with formation of anionic σH adducts. Subsequent base-induced β-elimination of HCl proceeds selectively to give nitrobenzylic α-fluorocarbanions and, upon protonation, ethyl α-fluoro-α-nitroarylacetates.
doi_str_mv	10.1021/acs.joc.6b02219
format	Article
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title	Synthesis of α‑Fluoro-α-nitroarylacetates via Vicarious Nucleophilic Substitution of Hydrogen
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