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Synthesis 1988; 1988(12): 1007-1009
DOI: 10.1055/s-1988-27789
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A Simple and Efficient Synthesis of Alkyl (2-Nitroaryl)acetates and Alkyl 2-(2-Nitroaryl)propanoates via Vicarious Nucleophilic Substitution of Hydrogen in Nitroarenes by Carbanions or Alkyl Chloroacetates of Alkyl 2-Chloropropanoates

B. Mudryk* , M. Mąkosza
  • *Institute of Organic Chemistry, Polish Academy of Science, ul. Kasprzaka 44/52, PL 01-224 Warsaw, Poland
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Publication Date:
20 August 2002 (online)

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Alkyl chloroacetates react with nitroarenes and potassium tert-butoxide in dimethylformamide according to the Vicarious Nucleophilic Substitution pattern, preferentially in the position ortho to the nitro group, giving alkyl (2-nitroaryl)acetates in usually good yields. Alkyl 2-(2-nitroaryl) propanoates are obtained in an analogous manner.