[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:12][C:13]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16].Cl>ClC1C=CC=CC=1Cl.C1(C)C=CC=CC=1>[CH3:22][C:20]1[CH:19]=[CH:18][C:14]([C:15](=[O:16])[C:9]2[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=2)=[C:13]([CH3:12])[CH:21]=1To a suspension of anhydrous aluminum chloride (16.2 g) dispersed in 1,2-dichlorobenzene (150 ml) was added fluorobenzene (13 g), and thereto was added dropwise 2,4-dimethylbenzoyl chloride (17.0 g) at 0-20° C. The mixture was stirred at 10-30° C. for 1 hr and heated to 80° C. The mixture was stirred for 1 hr, cooled again and poured into 6N hydrochloric acid. The reaction mixture was diluted with a great excess toluene and partitioned. The obtained organic layer was washed successively with 5% aqueous sodium hydroxide solution and water, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography using cyclohexane-ethyl acetate as eluent to give nearly pure 1,3-dimethyl-4-(4′-fluorobenzoyl)benzene (19.4 g, 85%) as pale-yellow oil. The spectrum data of this oil were the same as those confirmed in Example 7.
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