Nitrobenzene → N,N-diphenyl-10-[10-(N-phenylanilino)anthracen-9-yl]anthracen-9-amine

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Reaction Steps

In a flask were placed 35 g of 9,9′-bianthryl and 300 mL of carbon tetrachloride, and to the vigorously stirred mixture was slowly added 40 g of bromine under cooling. After addition, the mixture was slowly warmed and then refluxed for 1 hour with stirring. Carbon tetrachloride was evaporated from the reaction mixture under a reduced pressure, the residual solid was extracted with carbon tetrachloride using a Soxhlet extractor. The extract was dried and concentrated to give 42 g(yield 81%) of 10,10′-dibromo-9,9′-bianthryl. Then, in a 100 mL three-necked flask were placed 25 g of 10,10′-dibromo-9,9′-bianthryl, 20 g of diphenylamine, 17 g of potassium carbonate, 0.4 g of copper powder and 80 mL of nitrobenzene, and the mixture was stirred at 200° C. for 30 hours. After completion of the reaction, toluene was added to the mixture. The mixture was filtered to remove inorganics. Toluene and nitrobenzene were evaporated under a reduced pressure. The residue was purified by column chromatography on silica gel eluting with a 1:2 mixture of toluene and ligroin, to give 19 g(yield: 55%) of 10,10′-bis(diphenylamino)-9,9′-bianthryl.

Provenance & Evidence