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OPPI BRIEFS

SYNTHESIS OF 2-HALO-4,5-DIFLUOROBENZOIC ACIDS

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Pages 655-658 | Received 09 May 1991, Published online: 18 Feb 2009

References

  • Bitha , T. and Lin , Y. I. U. S. Patent . 4,833,270 . May 23, 1989 . From 5,6-difluoroisatin see Chem. Abs., 111, 173772s (1989). From 1-bromo-2,4,5-trifluorobenzene, see Japanese Patent SH058–150543; Chem. Abs., 100, 51279p (1984). From 2,4,5-trifluorobenzotrifluoride, see Japanese Patent SHO62–108839; Chem. Abs., 108, 37390b (1988). From dichlorophthalic anhydride, see M. J. Fifolt and A. M. Foster, U. S. Patent 4,374,266 and 4,374,267; Chem. Abs., 97, 197986h (1982). From 1-bromo-2,4,5-trifluorobenzene, see A. J. Bridges, W. C. Patt, and T. M. Stickney, J. Org. Chem., 55, 773(1990)
  • O'Rielly , N. J. , Derwin , W. S. , Fertel , L. B. and Lin , H. C. 1990 . Syn. Lett. , 1 : 609
  • O'Rielly , N. J. , Derwin , W. S. and Lin , H. C. 1990 . Syn. Lett. , 1 : 339
  • Finger , G. C. and Kruse , C. W. 1956 . J. Am. Chem. Soc. , 78 : 6043
  • This aniline tends to air oxidize rapidly. This was avoided by filtering the reaction mixture under an inert atmosphere at 0°
  • Doyle , M. P. and Bryker , W. J. 1979 . J. Org. Chem. , 44 : 1572
  • Schiemann , G. 1934 . J. prakt. Chem. , 140 : 97 in this paper, 1,2,4-trifluorobenzene was obtained in 3% yield by nitration of 1,4-difluorobenzene followed by reduction, diazotization and pyrolysis.
  • When α-chloroacetyl chloride was used, the yields were about 95% in both cases. These α-haloacetophenones are oxidized by bleach to give the benzoic acids also in similar yields
  • House , H. O. 1972 . “Modern Synthetic Reactions” , 2nd ed , 464 New York, NY : W. A. Benjamin .
  • The procedures used are similar to those reported in European patent application # 303,291; Chem. Abs., 111, 77647j (1989)
  • DeGraw , J. I. and Corey , M. 1968 . J. Chem. Eng. Data , 13 : 587

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