[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.[CH3:16][Si:17]([CH3:20])([CH3:19])Cl.S(=O)(=O)(O)O>BrCCCCCCC1C=CC(Cl)=CC=1.O1CCCC1.COC(C)(C)C.[Li+].[Li+].[Cl-].[Cl-].[Cl-].[Cl-].[Cu+2]>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH:8]([Si:17]([CH3:20])([CH3:19])[CH3:16])[CH2:7][CH2:6][CH2:5][CH2:4][CH3:3])=[CH:10][CH:11]=1Approximately 2 g (82 mMol) of magnesium in a flask were moistened with tetrahydrofuran. A Grignard reaction was initiated using 5 drops of 1-(6-bromohexyl)-4-chlorobenzene. The remainder of a total of 17 g of the halogen compound (61 mMol), dissolved in 50 ml of tetrahydrofuran, was added dropwise at 50° to 60° C. When the addition was complete, the mixture was kept at this temperature for an additional 2.5 hours, and a solution of 12 g (110 mMol) of trimethylchlorosilane and a catalytic amount of dilithium tetrachlorocuprate in 40 ml of tetrahydrofuran was then added dropwise at 20° to 40° C. The mixture was stirred at 60° C. for 1 hour, then allowed to stand overnight and diluted with 200 ml of tert-butyl methyl ether. The mixture was then acidified using 2N sulfuric acid, the phases were separated, and the organic phase was washed and dried. The evaporated residue was fractionated. About 6.4 g of 1-chloro-4-(1-trimethylsilylhexyl)benzene (38.6 percent yield) were obtained at a pressure of 0.2 hPa and at 88° to 90° C.
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