[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[F:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1>C1COCC1>[F:17][C:18]1[CH:19]=[C:20]([C:7]2[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=2)[CH:21]=[CH:22][CH:23]=1In a nitrogen atmosphere, a solution prepared by mixing 50.00 g of 4-propylbromobenzene, 0.87 g of tetrakis-triphenylphosphine palladium, 60 mL of an aqueous potassium carbonate solution (2 mol/L), and 150 mL of THF was heated to 60° C., and 35.14 g of 3-fluorophenylboronic acid was added to the solution over 20 minutes. After the resultant mixture was stirred at 60° C. for 3 hours, the mixture was allowed to cool, and an organic layer was separated by adding hexane. The organic layer was washed with saturated brine and dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure. As a result of purification by silica gel column chromatography, 44.32 g of 3-fluoro-1-(4-propylphenyl)benzene was produced.
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