The α-halogenated pyridines react with potassium fluoride in various solvents to give replacement of the α-halogen by fluorine. A 50% yield of 2-fluoropyridine was obtained from 2-chloropyridine by heating with potassium fluoride in dimethyl sulfone or tetramethylene sulfone for twenty-one days; 2-bromopyridine gave a similar yield with a heating period of only seven days. The α-halogens of the polyhalopyridines undergo the exchange reaction more readily than do the halogens of the α-monohalopyridines. The proposed structures of the fluoropyridines are supported by alternate syntheses and by n.m.r. studies. © 1963, American Chemical Society. All rights reserved.
CITATION STYLE
Finger, G. C., Starr, L. D., Dickerson, D. R., Gutowsky, H. S., & Hamer, J. (1963). Aromatic Fluorine Compounds. XI. Replacement of Chlorine by Fluorine in Halopyridines. Journal of Organic Chemistry, 28(6), 1666–1668. https://doi.org/10.1021/jo01041a058
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