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Synthesis 1989; 1989(12): 905-908
DOI: 10.1055/s-1989-27427
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Syntheses of 2-Chloro- and 2-Amino-5-fluoropyridines and Isolation of a Novel Difluoroboryl Imidate

Elli Smakula Hand* , David C. Baker
  • *Department of Chemistry, The University of Alabama, Tuscaloosa, AL 35487-0336, USA
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Publication Date:
02 May 2002 (online)

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The highly volatile, weakly basic 2-chloro-5-fluoropyridine (3), prepared by diazotization of 5-amino-2-chloropyridinc (1) with isoamyl nitrite/tetrafluoroboric acid followed by thermolysis (70%) has been characterized. Reaction of 3 with ammonia afforded a 3:1 mixture (40%) of 1 and 2-amino-5-fluoropyridine (4). An alternate, 5-step synthesis gave 4 in 33% overall yield from 2-amino-5-nitropyridine (5). One of the intermediates was shown to have a novel difluoroboryl imidate 10 structure.

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