Synthesis of bis(ether nitrile)s and bis(ether acid)s from simple aromatic diols bymeta-fluoro displacement from 3-fluorobenzonitrile

Abstract

There is interest in synthesizing bis(ether acid)s and related compounds to use as monomers in order to prepare processable aromatic polymers, such as poly(ether amide)s and poly(ether ester)s. We have now found that it is possible to prepare efficiently bis(3-cyanophenoxy)phenylenes by fluoro displacement from 3-fluorobenzonitrile and phenylene diols or their derivatives, such as substituted catechols, and to convert 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 ester)s. Themeta-fluoro displacement is performed at elevated temperatures in N-methylpyrrolidinone.