Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.O>[F:13][C:14]1[CH:15]=[C:16]([C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:6][CH:7]=2)[CH:17]=[CH:18][CH:19]=11-Bromo-4-pentylbenzene (T-1; 50.0 g), 3-fluorophenylboronic acid (31.4 g), potassium carbonate (91.2 g), Pd(Ph3P)2Cl2 (4.63 g), toluene (150 ml), Solmix A-11 (150 ml), and water (150 ml) were added to a reaction vessel under a nitrogen atmosphere, and heated under reflux for 3 hours. The reaction mixture was cooled to 25° C., and then poured into water (500 ml) and toluene (500 ml) and mixed. Then, the mixture was allowed to stand to be separated into two layers of organic and aqueous layers, and the extraction to an organic layer was carried out. The obtained organic layer was fractionated, washed with water, and then dried over anhydrous magnesium sulfate. The obtained solution was concentrated under reduced pressure, and the residue was purified with a fractional operation by means of column chromatography using heptane as the eluent and silica gel as the stationary phase powder. The product was further purified by recrystallization from Solmix A-11 and dried, whereby 45.2 g of 3-fluoro-4′-pentylbiphenyl (T-2) was obtained. The yield based on the compound (T-1) was 85%.
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