[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([Li])(CC)C.[I:22]I>C1(C)C=CC=CC=1.C1COCC1.CCCCCC.C1CCCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)[CH:5]=[CH:6][C:7]=1[I:22]To a reaction vessel under a nitrogen atmosphere, 3-fluoro-4′-propylbiphenyl (T-1) (23.1 g) and THF (250 ml) were added, and cooling was carried out to −74° C. Thereto, a sec-butyllithium (1.06 M), cyclohexane, n-hexane solution (122 ml) was added dropwise in a temperature range of −74° C. to −70° C., and stirring was carried out for another 2 hours. Subsequently, a THF (200 ml) solution of iodine (35.6 g) was added dropwise in a temperature range of −75° C. to −70° C., and stirring was carried out for 6 hours while returning to room temperature. The resultant reaction mixture was poured into ice water (500 ml), and mixing was carried out. Toluene (400 ml) was added to separate layers into an organic layer and an aqueous layer, and an extraction operation was performed. The resultant organic layer was sequentially washed with an aqueous solution of sodium thiosulfate and water, and drying over anhydrous magnesium sulfate was carried out. The resultant solution was concentrated under reduced pressure, and a residue was purified by means of column chromatography (silica gel; heptane), and further purified by recrystallization from Solmix A-11, and thus 3-fluoro-4-iodo-4′-propylbiphenyl (T-2) (25.4 g) was obtained. The yield based on compound (T-1) was 69%.
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