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Synlett 1991; 1991(3): 181-182
DOI: 10.1055/s-1991-21979
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Synthesis of (Nitroaryl)chloromethanes via Vicarious Nucleophilic Substitution of Hydrogen

Mieczysław Makosza* , Maciej Białecki
  • *Institute of Organic Chemistry, Polish Academy of Sciences, ul.Kasprzaka 44/52, PL-01-225 Warszawa, Poland
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Publication Date:
07 March 2002 (online)

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Vicarious Nucleophilic Substitution of hydrogen in nitroarenes by tert-butyl dichloroacetate anion gives tert-butyl (nitroaryl)chloroacetates. These are converted either by mild hydrolysis in formic acid followed by decarboxylation in refluxing dimethylformamide or by a one-pot hydrolysis-decarboxylation in refluxing acetic acid to (nitroaryl)chloromethanes in high yield.