Hydrochloric Acid → 2,2'-Bis-(trifluoromethyl)-4-iodo-4'-nitro-1,1'-biphenyl

Participants

Reaction Steps

Starting materials useful in the manufacture of substituted-quaterphenylene polyamides of the invention can be prepared by resort to a variety of organic synthetic routes. Preferred polyamides of the invention can be prepared, for example, by reaction of terephthaloyl chloride and/or trans-p,p'-stilbene dicarbonyl chloride with the diamino compound, 4,4'"-diamino-2,2',3",2'"-tetrakis(trifluoromethyl)-1,1':4',1'"-quaterphenyl. This novel diamine can be prepared, for example, from 2-bromo-5-nitro-benzotrifluoride by resort to the following reactions: (a) an Ullmann coupling of 2-bromo-5-nitrobenzotrifluoride utilizing active copper and dimethylformamide to provide 2,2'-bis-(trifluoromethyl)-4,4'-dinitro-1,1'-biphenyl; (b) a partial reduction utilizing aqueous sodium hydrosulfide to 4-amino-2,2'-bis-(trifluoromethyl)-4'-nitro-1,1'-biphenyl; (c) a diazotization of the resulting amine utilizing aqueous sodium nitrite and hydrochloric acid and a Sandmeyer reaction of the resulting diazonium salt with potassium iodide to provide 2,2'-bis-(trifluoromethyl)-4-iodo-4'-nitro-1,1'-biphenyl; (d) an Ullmann coupling of the resulting biphenyl compound utilizing active copper for production of 4,4'"-dinitro-2,2',3",2'"-tetrakis-(trifluoromethyl)-1,1':4',1":4",1'"-quaterphenyl; and (e) a reduction utilizing stannous chloride and hydrochloric acid for production of the desired diamine starting material. The production of this diamine starting material is illustrated by the following reaction sequence: ##STR32##

Provenance & Evidence