Reactions of 4,5-difluoro-1,2-dinitrobenzene with amines in dimethylformamide or EtOH

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Substitution reactions of 1,2-difluoro-4,5-dinitrobenzene were explored in dimethylformamide alone and with KOH/H2O, Hünig?s base or Et3N and with Me2NHCl/Et3N in EtOH. The fluorine atoms were always displaced in preference to the nitro groups. Three compounds were prepared from these studies and were characterised by X-ray single crystal structure determinations.
Original languageEnglish
Pages (from-to)1-8
Number of pages8
JournalJournal of Chemical Research
Issue number1
Early online date20 Feb 2023
Publication statusPublished - Feb 2023

Bibliographical note

We thank the UK EPSRC National Mass Spectrometry Service Centre for mass spectrometric data and the UK National Crystallography Centre (University of Southampton) for the X-ray data collections. MJ Plater performed all synthesis and obtained the characterisation data and WTA Harrison solved the crystallographic data sets. Data sets were obtained free of charge from the National Crystallography Centre, Southampton University

The author(s) received no financial support for the research, authorship, and/or publication of this article.


  • 4,5-difluoro-1,2-dinitrobenzene
  • fluoride
  • Hofmann elimination
  • Hünig’s base
  • nucleophilic substitution


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