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Aromatic fluorine compounds. XI. Replacement of chlorine by fluorine in halopyridines

Journal of Organic Chemistry

By:
, , , ,
DOI: 10.1021/jo01041a058

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Abstract

The ??-halogenated pyridines react with potassium fluoride in various solvents to give replacement of the ??-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 ??-halogens of the polyhalopyridines undergo the exchange reaction more readily than do the halogens of the ??-monohalopyridines. The proposed structures of the fluoropyridines are supported by alternate syntheses and by n.m.r. studies.

Additional Publication Details

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
Larger Work Type:
Article
Larger Work Subtype:
Journal Article
Larger Work Title:
Journal of Organic Chemistry
First page:
1666
Last page:
1668
Number of Pages:
3