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Electrochemical fluorination of aromatic compounds in anhydrous HF

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Abstract

Electrochemical fluorination of anisole furnished 2-and 4-fluoroanisoles in a 3:1 ratio, guaiacol, and 4,4′-dimethoxydiphenyl ether. Phenylacetonitrile alongside the fluorination in the ring suffered the transformation of the cyano group into a trifluoromethyl. 4-Bromobenzamide was fluorinated to a high conversion mostly in the ring to afford predominantly 4-bromo-3,3,6,6-tetrafluoro-1,4-cyclohexadienecarboxamide. 4-Bromonitrobenzene in a low yield gave 4-bromofluoronitrobenzene and 3,4-dibromofluoronitrobenzene. 3-Bromo-nitrobenzene and 1,4-dichlorobenzene lid not undergo fluorination. In the course of the electrolysis of the 4-bromobenzamide and 4-bromonitrobenzene in anhydrous HF apart the fluorination occurred also the bromination of the substrates.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, 664033, Russia

    B. A. Shainyan & Yu. S. Danilevich

Authors
  1. B. A. Shainyan
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  2. Yu. S. Danilevich
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Correspondence to B. A. Shainyan.

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Original Russian Text © B.A. Shainyan, Yu.S. Danilevich, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, no. 2, pp. 231–235.

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Shainyan, B.A., Danilevich, Y.S. Electrochemical fluorination of aromatic compounds in anhydrous HF. Russ J Org Chem 42, 214–219 (2006). https://doi.org/10.1134/S1070428002120096

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  • DOI: https://doi.org/10.1134/S1070428002120096

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