2,2'-Bis(trifluoromethyl)-4,4'-dinitrobiphenyl → 2,2'-Bis(trifluoromethyl)-4-nitro-4'-amino-biphenyl

Participants

Reaction Steps

This example illustrates the preparation of poly-2,2'(bis-trifluoromethyl)-4,4'-biphenylene carboxamide, i.e., a polymer having the following recurring structural units: ##STR51## The polymer was prepared by polymerization (as described hereinafter) of the monomer 2,2'-bis(trifluoromethyl)-4-amino-4-biphenylcarboxylic acid having the structure ##STR52## This monomer was prepared from 2,2'-bis(trifluoromethyl)-4,4'-dinitro-biphenyl by partial reduction using sodium hydrogen sulfide to provide 2,2'-bis(trifluoromethyl)-4-nitro-4'-amino-biphenyl; diazotization of the resulting compound followed by reaction with sodium triiodide to provide 2,2'-bis(trisfluoromethyl)-4-nitro-4'-iodo-biphenyl; a Rosenmund-von Braun reaction using cuprous cyanide in N-methyl-2-pyrrolidone to provide 2,2'-bis(trifluoromethyl)-4-nitro-4'-cyano-biphenyl; hydrolysis using 63% sulfuric acid to provide 2,2'-bis(trifluoromethyl)-4-nitro-4'-biphenyl carboxylic acid; and catalytic reduction using palladium on carbon to provide the aforesaid monomer 2,2'-bis(trifluoromethyl)-4-amino-4'-biphenyl carboxylic acid.

Provenance & Evidence