C(C1C=CC=CC=1)C.[F:9][C:10]1[C:17]([F:18])=[C:16](C#N)[C:15]([F:21])=[C:14]([F:22])[C:11]=1[C:12]#[N:13].[H][H]>[Pd]>[F:9][C:10]1[C:17]([F:18])=[CH:16][C:15]([F:21])=[C:14]([F:22])[C:11]=1[C:12]#[N:13]200 g of ethylbenzene, 0.30 g of 5% palladium/activated carbon, and 6.0 g of 2,3,5,6-tetrafluoroterephthalonitrile were added to a 1000 cc stainless steel autoclave in a nitrogen atmosphere. The gas phase was sufficiently replaced with a mixed gas of 41 vol % hydrogen and 59 vol % nitrogen, then the mixed gas was used to keep the pressure at 0.23 MPa and the temperature was maintained at 190° C. After 2, 4, and 6 hours, the reaction solution was analyzed by gas chromatography, whereupon the conversions of 2,3,5,6-tetrafluoroterephthalonitrile were found to be 23, 62, and 99% and the yields of 2,3,5,6-tetrafluorobenzonitrile (based on 2,3,5,6-tetrafluoroterephthalonitrile) were 22, 56, and 87%, respectively.
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