2,2'-Bis(trifluoromethyl)-4,4'-dinitrobiphenyl → 2,2'-Bis(trifluoromethyl)-4-nitro-4'-amino-biphenyl
Reaction equation
FC(F)(F)C1CC(N)(C(O)=O)C=CC=1C1C=CC=CC=1C(F)(F)F.[F:25][C:26]([F:50])([F:49])[C:27]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=1[C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-])=O)=[CH:38][C:37]=1[C:45]([F:48])([F:47])[F:46].S.[Na]>>[F:25][C:26]([F:49])([F:50])[C:27]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=1[C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][C:37]=1[C:45]([F:46])([F:47])[F:48]Participants
Procedure
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.
Sources & evidence
- ORD record
- ord-789dac5d90ca4409b87e2de3dfdc06ec
- Source dataset
- uspto-grants-1984_07
- Patent number
- US04461886
Reaction notes
Loading…