[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O[Na])(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C(C)=CC=CC=1>[C:15]1([C:10]2[C:11]3[NH:12][C:13]4[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=4)[C:6]=3[CH:7]=[CH:8][CH:9]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Ina stream of argon, 670 g of carbazole, 850 kg of iodobenzene, 20 L of xylene, 460 g of t-BuONa, and palladium acetate (Pd(OAc)2) were added, and then the mixture was refluxed for 8 hours. Impurities were filtrated, and then the filtrate was concentrated under reduced pressure and washed with hexane. After that, the washed product was dried. As a result, 820 g of phenylcarbazole were obtained as a white powder. In a stream of argon, 24 g of phenylcarbazole, 8.3 g of potassium iodide, 10.7 g of potassium iodate, 500 mL of ethanol, and 8 mL of sulfuric acid were added into a 1,000-mL three-necked flask, and then the mixture was stirred at 75° C. for 2 hours. After that, the reaction product was injected into ice water, and then the mixture was extracted with ethyl acetate and water. After having been washed with water, the extract was subjected to column chromatography with silica gel. As a result, 67 g of a white powder were obtained. A reaction was performed in the same manner as in the synthesis of Intermediate 1 except that 9-phenylcarbazole was used instead of 4-bromobiphenyl. As a result, 22.3 g of a white powder were obtained. FD-MS analysis identified the powder as Intermediate 11.
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