3-Cyano-2,4,5-trifluorobenoxyl fluoride and intermediate...

Details 3-Cyano-2,4,5-trifluorobenoxyl fluoride and intermediate... 3-Cyano-2,4,5-trifluorobenoxyl fluoride and intermediate...

2007-09-11

2007-09-11

Oh, Taylor Victor (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitriles

C562S459000, C562S458000, C570S127000, C570S210000

Reexamination Certificate

active

10749593

ABSTRACT:
The present invention relates to 3-cyano-2,4,5-trifluorobenzoyl fluoride and to intermediates for its preparation and to the process for the preparation of 3-cyano-2,4,5-trifluoro-benzoyl fluoride, which starts from 5-fluoro-1,3-xylene (VIII); which is bichlorinated in the ring in the presence of a catalyst under ionic conditions to give 2,4-dichloro-5-fluoro-1,3-dimethylbenzene (VII). The latter is chlorinated in the side chains under free-radical conditions to give 2,4-dichloro-5-fluoro-3-dichloromethyl-1-trichloromethylbenzene (VI). The latter is hydrolysed via 2,4-dichloro-5-fluoro-3-dichloromethylbenzoic acid (V), which can be isolated if necessary, to give 2,4-dichloro-5-fluoro-3-formyl-benzoic acid (IV), the aldehyde group of which is reacted to give 2,4-dichloro-5-fluoro-3-N-hydroxyiminomethyl-benzoic acid (III), from which, with simultaneous conversion of the carboxyl group into the chlorocarbonyl group, water is eliminated using an acid chloride to give the nitrile 2,4-dichloro-3-cyano-5-fluoro-benzoyl chloride (II). Finally, the nitrile is subjected to fluorine/chlorine exchange.

REFERENCES:
patent: 3615767 (1987-11-01), None
patent: 3702393 (1998-08-01), None
patent: 0307897 (1989-03-01), None
patent: 9731001 (1997-08-01), None

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