Tetrafluoro-N-phenylphthalimide

Details Tetrafluoro-N-phenylphthalimide Tetrafluoro-N-phenylphthalimide

1989-02-27

1991-09-10

Rotman, Alan L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

562480, C07D20948, C07C 6300, A61K 3140

Patent

active

050475533

ABSTRACT:
Chlorinated phthalic anhydrides are converted to fluorinated phthalic acids without dilactone formation by reacting an anhydride with a primary amine under anhydrous conditions to form the corresponding chlorinated-N-substituted phthalimide which in turn is reacted with a fluorinating agent under anhydrous conditions to form the corresponding fluorinated phthalimide which is hydrolyzed to form the corresponding fluorinated phthalic acid.
In a preferred embodiment tetrachlorophthalic anhydride is refluxed with aniline in the presence of glacial acetic acid for 5 to 10 hours to form tetrachloro-N-phenylphthalimide which is reacted with KF in sulfolane in the presence of tributylhexadecylophosphonium bromide under nitrogen at 140.degree. C. to 160.degree. C. for 10 to 15 hours to form tetrafluoro-N-phenylphthalimide which in turn is hydrolyzed by refluxing with 50% H.sub.2 SO.sub.4 for 15 to 25 hours. The tetrafluoro-N-phenylphthalimide is a novel compound.
The fluorinated phthalic acid products are intermediates for the corresponding fluorinated phthalic anhydrides, fluorinated benzoic acids and fluorinated benzenes.

REFERENCES:
patent: 4769493 (1988-09-01), Ito et al.

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