Aromatic fluorine compounds. XI. Replacement of chlorine by fluorine in halopyridines
Journal of Organic Chemistry
By: G. C. Finger, L. D. Starr, D. R. Dickerson, H. S. Gutowsky, and J. Hamer
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Abstract
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.
| Publication type | Article |
|---|---|
| Publication Subtype | Journal Article |
| Title | Aromatic fluorine compounds. XI. Replacement of chlorine by fluorine in halopyridines |
| Series title | Journal of Organic Chemistry |
| DOI | 10.1021/jo01041a058 |
| Volume | 28 |
| Issue | 6 |
| Year Published | 1963 |
| Language | English |
| Publisher | American Chemical Society |
| Description | 3 p. |
| First page | 1666 |
| Last page | 1668 |
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