Aromatic fluorine compounds. XI. Replacement of chlorine by fluorine in halopyridines
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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.
Suggested Citation
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, v. 28, no. 6, p. 1666-1668, https://doi.org/10.1021/jo01041a058.
| 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 |
| Publication Date | May 01, 2002 |
| Year Published | 1963 |
| Language | English |
| Publisher | American Chemical Society |
| Description | 3 p. |
| First page | 1666 |
| Last page | 1668 |