SYNTHESIS OF BIS(ETHER NITRILE)S AND BIS(ETHER ACID)S FROM SIMPLE AROMATIC DIOLS BY META-FLUORO DISPLACEMENT FROM 3-FLUOROBENZONITRILE

There is interest in synthesizing bis(ether acid)s and related compoun ds to use as monomers in order to prepare processable aromatic polymer s, such as poly(ether amide)s and poly(ether ester)s. We have now foun d that it is possible to prepare efficiently bis(3-cyanophenoxy)phenyl enes by fluoro displacement from 3-fluorobenzonitrile and phenylene di ols or their derivatives, such as substituted catechols, and to conver t those bis(ether nitrile)s to bis(3-carboxyphenoxy) phenylenes which can be used in the synthesis of poly(ether amide)s and poly(ether este r)s. The meta-fluoro displacement is performed at elevated temperature s in M-methylpyrrolidinone.