Aromatic fluorine compounds. XI. Replacement of chlorine by fluorine in halopyridines
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.
Citation Information
Publication Year | 1963 |
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Title | Aromatic fluorine compounds. XI. Replacement of chlorine by fluorine in halopyridines |
DOI | 10.1021/jo01041a058 |
Authors | G.C. Finger, L. D. Starr, D. R. Dickerson, H. S. Gutowsky, J. Hamer |
Publication Type | Article |
Publication Subtype | Journal Article |
Series Title | Journal of Organic Chemistry |
Index ID | 70010835 |
Record Source | USGS Publications Warehouse |