Heterocyclic polyfluoro-compounds. Part XXI. Synthesis of some 2-substituted tetrafluoropyridines: 2,3,4,5-tetrafluoro-6-methoxypyridine and 3,4,5,6-tetrafluoropyridine-2-carbaldehyde, -2-carboxylic acid,-2-carboxamide, and -2-carbonitrile
- 1 January 1974
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2367-2369
- https://doi.org/10.1039/p19740002367
Abstract
3,4,5,6-Tetrafluoropyridine-2-carbonitrile and 3,5-dichloro-4,6-difluoropyridine-2-carbonitrile can be obtained by heating 3,4,5,6-tetrachloropyridine-2-carbonitrile with potassium fluoride. Reduction of the tetrafluorocompound with Raney alloy–aqueous formic acid yields 3,4,5,6-tetrafluoropyridine-2-carbaldehyde (characterised as its oxime), which reacts with oxygen to give 3,4,5,6-tetrafluoropyridine-2-carboxylic acid (perfluoropicolinic acid); acidic hydrolysis of tetrafluoropyridine-2-carbonitrile provides 3,4,5,6-tetrafluoropyridine-2-carboxamide.Treatment of phenyl 2,3,5,6-tetrafluoropyridyl sulphone with sodium methoxide yields phenyl 2,3,5-trifluoro-6-methoxypyridyl sulphone, which reacts with caesium fluoride in hot tetramethylene sulphone to give 2,3,4,5-tetrafluoro-6-methoxypyridine.Keywords
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