[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[CH2:10]([C:14]1[CH:19]=[CH:18][C:17](Cl)=[CH:16][CH:15]=1)[CH2:11][CH2:12][CH3:13].[Cl-].C(C1C=CC=C(C(C)C)C=1[NH+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C1)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCCCC.C1COCC1>[CH2:10]([C:14]1[CH:19]=[CH:18][C:17]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:16][CH:15]=1)[CH2:11][CH2:12][CH3:13]Using a THF solution of 4-fluorophenylmagnesium bromide (1.46 mL, 1.03 M, 1.5 mmol), 4-butylchlorobenzene (168.7 mg, 1.0 mmol), FeF3.3H2O (8.34 mg, 0.05 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride (63.8 mg, 0.15 mmol) and triphenylphosphine (13.1 mg, 0.05 mmol) as starting materials, the reaction was performed at a scale of 1.0 mmol at 60° C. for 24 hours, then at 80° C. for 12 hours in the same manner as in Example 15. After performing silica gel chromatography (pentane), the above compound was obtained as a white solid (0.201 g, yield=88%, purity=>98% (GC analysis)).
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