Br[C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[Li]CCCC.[I:27]I.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[I:27][C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2
3.33 g (10 mmol) of 9-bromo-10-phenylanthracene was dissolved in 80 ml of tetrahydrofuran (abbreviation: THF), and the temperature was lowered to −78° C. 7.5 ml (12.0 mmol) of n-BuLi (1.6M) was dropped into the reaction solution by a dropping funnel, and it was stirred for 1 hour. A solution in which 5 g (20.0 mmol) of iodine was dissolved in 20 ml of THF was dropped and stirred for 2 hours at −78° C. After reaction, a sodium thiosulfate water solution was added to stop the reaction. An organic layer was washed with a sodium thiosulfate water solution and a saturated saline and dried with magnesium sulfate. After the natural filtration, the filtrate was concentrated and the obtained solid was recrystallized by ethanol. Then, 3.1 g of a light-yellow solid of 9-iodo-10-phenylanthracene, which was the intended object, was obtained with a yield of 83% (synthetic scheme of (b-5)).
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