C1CCCCC1.C([Li])(CC)C.[F:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[CH:16]=[CH:17][CH:18]=1.[I:31]I>O.C1COCC1>[F:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[CH:16]=[CH:17][C:18]=1[I:31]
A 53.35 ml cyclohexane solution of sec-butyl lithium in a concentration of 1.01M was dropped into a 200 ml THF solution of 8.43 g (33.68 mmol) of the above 2-[2-(3-fluorophenyl)ethyl]naphthalene at −70° C. After the dropping was finished, the reaction solution was stirred at the same temperature for 1 hour, added with a 200 ml THF solution of 13.68 g (=53.90 mmol) of iodine through dropping and then slowly heated to room temperature. After being stirred for 18 hours, the reaction solution was added in iced water dissolved with Na2S2O3.5H2O, and then the reaction mixture was extracted twice with toluene. The extract was washed thrice with water, and was then dried with anhydrous MgSO4. After the solvent was evaporated under a reduced pressure, the obtained orange solid of 13.05 g was purified with silica gel chromatography using heptane/toluene in a ratio of 5:1 as the eluent to obtain a yellowish solid of 11.66 g, which was recrystallized with a mixed solvent of Solumix/heptane in a ratio of 5:1 to obtain 10.60 g of 2-[2-(3-fluoro-4-iodophenyl)ethyl]naphthalene as yellowish crystals.
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