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New synthesis routes to 2‐halopyridines. III. 2‐fluoropyridine
Author(s) -
Boudakian Max M.
Publication year - 1967
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570040314
Subject(s) - chemistry , yield (engineering) , alkali metal , pyridine , potassium , fluoride , solvent , potassium fluoride , sodium , inorganic chemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , metallurgy
The solvent‐free fluorination of 2‐chloropyridine (III) with alkali metal fluorides and bifluorides was investigated. While complete degradation occurred with potassium fluoride at 315°, the use of potassium bifluoride under identical conditions provided a 74% yield of 2‐fluoro‐pyridine (II). Sodium bifluoride gave only a 3.5% yield of the desired product. These results are discussed in the light of: activation of the substrate, properties of the fluorinating agents, and the stability of 2‐fluoropyridine.