Chlorination and decarboxylation of (heptafluoronaphthalen-2-yl)acetic acid. Synthesis of 2-(dichloromethyl)- and 2-(difluoromethyl)heptafluoronaphthalenes


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Abstract

Decarboxylation of (heptafluoronaphthalen-2-yl)acetic acid in DMF in the presence of NaHCO3 gave 2-methylheptafluoronaphthalene, and treatment with PCl5 on heating afforded dichloro(heptafluoronaphthalen-2-yl)acetic acid. Decarboxylation of the latter in DMF led to the formation of 2-(dichloromethyl)-heptafluoronaphthalene which was converted to 2-(difluoromethyl)heptafluoronaphthalene by heating with cesium fluoride.

About the authors

V. R. Sinyakov

Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch

Email: karpov@nioch.nsc.ru
Russian Federation, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090

T. V. Mezhenkova

Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch

Email: karpov@nioch.nsc.ru
Russian Federation, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090

V. M. Karpov

Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch

Author for correspondence.
Email: karpov@nioch.nsc.ru
Russian Federation, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090

Ya. V. Zonov

Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch; Novosibirsk State University

Email: karpov@nioch.nsc.ru
Russian Federation, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090; ul. Pirogova 2, Novosibirsk, 630090

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