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Aromatic fluorine compounds. X. The 2,3- and 2,6-difluoropyridines

Journal of Organic Chemistry

By:
, , , and
DOI: 10.1021/jo01058a050

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Abstract

The preparation of difluoropyridines by the Schiemann reaction was investigated. 2-Amino-6-fluoropyridine (IIIa), necessary for the synthesis of 2,6-difluoropyridine (IVa) by the Schiemann reaction, was conveniently prepared by the Curtius degradation of 6-fluoropicolinic hydrazide (IIa) and by the Hofmann reaction on 6-fluoropicolinamide (IId). Since an ??-fluorine on a pyridine nucleus is preferentially replaced by hydrazine when it is either adjacent to or opposite a carbomethoxy group, the hydrazides necessary for the synthesis of 3-amino-2- and 6-fluoropyridine could not be prepared. These amines were prepared from the appropriate 2-fluoropyridinecarboxamide by the Hofmann reaction. The preparation of difluoropyridines was successful with two of the aminofluoropyridines and led to the following new compounds: 2,3-difluoro(IVb) and 2,6-difluoropyridine (IVa).

Additional Publication Details

Publication type:
Article
Publication Subtype:
Journal Article
Title:
Aromatic fluorine compounds. X. The 2,3- and 2,6-difluoropyridines
Series title:
Journal of Organic Chemistry
DOI:
10.1021/jo01058a050
Volume
27
Issue:
11
Year Published:
1962
Language:
English
Publisher:
American Chemical Society
Larger Work Type:
Article
Larger Work Subtype:
Journal Article
Larger Work Title:
Journal of Organic Chemistry
First page:
3965
Last page:
3968
Number of Pages:
4