Synthesis of deuterium labelled analogs of fluazifop and haloxyfop

✍ Scribed by Michael J. Bartels; Sterling C. Gatling

• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: French
• Weight: 228 KB
• Volume: 28
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580280214

✦ Synopsis

Abstract

Synthetic routes have been described for the preparation of stable isotope‐labelled analogs of two aryloxyphenoxypropionates, each containing approximately four deuterium atoms in the central phenyl ring of the molecule. Fluazifop‐2′,3′,5′,6′‐^2^H~4~ [2‐(4‐((5‐(trifluoromethyl)‐2‐pyridinyl)‐oxy)phenoxy)propionic acid‐2′,3′,5′,6′‐^2^H~4~] and haloxyfop‐2′,3′,5′,6′‐^2^H~4~ [2‐(4‐((3‐chloro‐5‐(trifluoromethyl)‐2‐pyridinyl)oxy)phenoxy)propionic acid‐2′,3′,5′,6′‐^2^H~4~] were synthesized from the common intermediate HPPA‐2′,3′,5′,6′‐^2^H~4~ [2‐(4‐hydroxyphenoxy)propionic acid‐2′,3′,5′,6′‐^2^H~4~]. This intermediate was obtained from HPPA via acid‐catalyzed deuterium exchange (^2^H~2~SO~4~ in ^2^H~2~O and CH~3~O^2^H).