Synthesis of 3-Cyano-2-fluoropyridines
Journal Article
·
· Journal of Fluorine Chemistry
OSTI ID:1038460
- ORNL
- N.D. Zelinsky Institute of Organic Chemistry
The synthesis of 3-cyano-2-fluoropyridines from readily available precursors was achieved via nucleophilic substitution of a leaving group in the 2-postion with KF or Bu4NF in polar aprotic solvents such as DMF and DMSO. Ionic tetrahydrothiophenium fragment is the most effective leaving group, the methanesulfonyl moiety is a somewhat less effective, and Brand Cl- are the least effective. Relatively mild conditions of the reaction between (2- pyridyl)-tetrahydrothiophenium salts and KF, as well as the convenience of one-step synthesis of these salts from 2(1H)-pyridinethiones, make these salts the compounds of choice for the preparation of ring-fluorinated pyridines.
- Research Organization:
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Sponsoring Organization:
- USDOE National Nuclear Security Administration (NNSA)
- DOE Contract Number:
- DE-AC05-00OR22725
- OSTI ID:
- 1038460
- Journal Information:
- Journal of Fluorine Chemistry, Vol. 130, Issue 2; ISSN 0022-1139
- Country of Publication:
- United States
- Language:
- English
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