Preparation of halogen analogs of picloram

Preparation of halogen analogs of picloram

Methods for preparing 5-fluoro-6-(bromo or chloro)picloram analogs, or derivatives thereof, from picloram acid, picloram ester, or the nitrile analog of picloram are provided. The methods include chemical process steps that: (1) introduce a phthaloyl group onto the 4-amino substituent of picloram ac...

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Hauptverfasser: Kister, Jeremy, Zhang, Chunming, Lin, Rongrong [Mandy], Irvine, Nicholas M, Niyaz, Noormohamed M, Tu, Siyu, Shinkle, Aaron A, Whiteker, Gregory T, Devaraj, Jayachandran, Lee, Melissa, Ling, Rong, Ghavtadze, Nugzar, Leng, Ronald B, Schuitman, Abraham D
Format: Patent
Sprache:eng
Schlagworte:
CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
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Zusammenfassung:Methods for preparing 5-fluoro-6-(bromo or chloro)picloram analogs, or derivatives thereof, from picloram acid, picloram ester, or the nitrile analog of picloram are provided. The methods include chemical process steps that: (1) introduce a phthaloyl group onto the 4-amino substituent of picloram acid, picloram ester, or the nitrile analog of picloram, (2) add 2 fluorine atoms at the 5,6-positions of the pyridine ring using halex fluorination chemistry, (3) remove the phthaloyl group, hydrolyze the ester or nitrile substituent, and add chlorine or bromine to the 6-position by treatment with an acid and water, and finally, (4) esterify the 5-fluoro-6-(bromo or chloro)picloram acid produced in step (3) to a 5-fluoro-6-(bromo or chloro)picloram ester.