Potassium Carbonate → N4,N4,N4'-Triphenyl-[1,1'-biphenyl]-4,4'-diamine

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4.3 g (17 mmol) of 4-bromodiphenylamine, 5 g (17 mmol) of triphenylamine-4-boronic acid, and 532 mg of tri(o-tolyl)phosphine were put into a 500 mL three-neck flask, and the atmosphere in the flask was substituted by nitrogen. 60 mL of toluene, 40 mL of ethanol, and 14 ml of a potassium carbonate aqueous solution (0.2 mol/L) were added into this mixture. The mixture was deaerated while being stirred under reduced pressure, and after deaeration, 75 mg (0.35 mmol) of palladium(II) acetate was added. This mixture was refluxed at 100° C. for 10.5 hours. An aqueous layer of the mixture was extracted with toluene. The extracted solution and an organic layer were washed together with saturated brine, and magnesium sulfate was added thereto for drying. This mixture was filtrated and the filtrate was concentrated to obtain an oily light-brown substance. The oily substance was dissolved in about 50 mL of toluene, and was subjected to suction filtration through Celite (manufactured by Celite Co., Ltd.), alumina, and Florisil (manufactured by Floridin Company). A solid substance obtained by concentrating the filtrate was purified by a silica gel column chromatography (developing solvent was a mixed solvent of hexane:toluene=4:6) to obtain a white solid substance. The obtained white solid substance was recrystallized with chloroform/hexane, so that 3.5 g of an white substance was obtained in yield 49%.

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