Br[C:2]1[CH:7]=[CH:6][C:5]([Si:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>C1C2C(=CC=CC=2)CCC1.[Cu]>[CH3:9][Si:8]([CH3:11])([CH3:10])[C:5]1[CH:6]=[CH:7][C:2]([N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[CH:13]2)=[CH:3][CH:4]=1To a 1L 3-neck flask equipped with a mechanical stir arm was added 14.5 g (65.1 mmol) of 1-bromo-4-trimethylsilylbenzene, 9.2 g (78.1 mmol) of benzimidazole, 9.1 g (143 mmol) of copper power, 31.4 g (228 mmol) of potassium carbonate, and 1.7 g (6.5 mmol) of 18-crown-6. These chemicals were stirred vigorously in 400 mL tetrahydronaphthalene at 180° C. under N2 atmosphere. After 20 hours of heating, the mixture was filtered warm. The solids on the funnel were repeatedly washed with dichloromethane to remove all organic products as filtrate. The mother liquor was then evaporated in vacuo and pooled with a small batch of crude material from a previous reaction. This residue was purified by distilling on a Kugelrohr apparatus twice. At 160° C., the removal of organic impurities was evidenced. At 200° C. the product distilled. Purification gave 14.2 g N-(p-trimethylsilylphenyl)benzimidazole as a white solid.
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