[C:1]1(=[O:16])[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4](=[O:15])[CH:3]=[CH:2]1.Br[CH2:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[CH:29](Br)Br.[I-].[Na+]>CN(C)C=O>[CH:27]1[C:28]2=[C:19]3[C:20](=[CH:21][CH:22]=[C:23]2[CH:24]=[CH:25][CH:26]=1)[CH:29]=[C:2]1[C:3]([C:4](=[O:15])[C:5]2[C:14]([C:1]1=[O:16])=[CH:13][C:12]1[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH:6]=2)=[CH:18]3In an atmosphere of argon, 6.9 g (33 mmole) of 1,4-anthraquinone, 9.8 g (25 mmole) of 1-(bromomethyl)-2-(dibromomethyl)naphthalene and 25 g (660 mmole) of sodium iodide were dissolved into 85 ml of dry dimethylformamide. After the exothermic reaction was completed, the reaction solution was heated to 70° C. and stirred for 8 hours. After the reaction was completed, the formed crystals were separated by filtration and washed with methanol and water and light yellow needle crystals of 8,15-benzo[a]pentacenequinone were obtained in the quantitative amount.
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