C1COCC1.[F:6][C:7]1[CH:12]=[CH:11][C:10]([Mg]Br)=[CH:9][CH:8]=1.[CH2:15]([C:19]1[CH:24]=[CH:23][C:22](Cl)=[CH:21][CH:20]=1)[CH2:16][CH2:17][CH3:18].[Cl-].C(C1C=CC=C(C(C)C)C=1[NH+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C1)(C)C>CCCCC>[CH2:15]([C:19]1[CH:24]=[CH:23][C:22]([C:10]2[CH:11]=[CH:12][C:7]([F:6])=[CH:8][CH:9]=2)=[CH:21][CH:20]=1)[CH2:16][CH2:17][CH3:18]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 (6.68 mg, 0.04 mmol) and 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride (51.2 mg, 0.12 mmol) as starting materials, the reaction was performed at a scale of 1.0 mmol at 60° C. for 24 hours in the same manner as in Example 2. After performing silica gel column chromatography (pentane), the above compound was obtained as a white solid (0.199 g, yield=87%, purity=>97% (GC analysis)).
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