II.[Mg].Br[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:11][Sn:12](Cl)([CH3:14])[CH3:13].[Cl-:16].[NH4+]>C(OCC)C>[Cl:16][C:5]1[CH:10]=[CH:9][C:8]([Sn:12]([CH3:14])([CH3:13])[CH3:11])=[CH:7][CH:6]=1A small quantity of iodine was put in a vessel containing 280 mg (12 mmol) of metal magnesium and 10 ml of anhydrous diethyl ether, and a solution of 2.0 g (10 mmol) of 4-bromobenzene in 10 ml of anhydrous diethyl ether was gradually added dropwise under stirring. Reaction progressed rapidly, and after the reaction somewhat calmed down, the mixture was heated and stirred at 50° C. for further 3 hours. Thereafter, the reactor was cooled to 0° C., 2.1 g (10 mmol) of trimethyltin chloride was added, and the mixture was heated again to 50° C. and refluxed for 2 hours. After the reaction, the reaction solution was cooled again to 0° C., saturated ammonium chloride solution was added, and the mixture was extracted with diethyl ether. The organic layer was washed with water and saturated saline, dried over anhydrous magnesium sulfate and anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane) and vacuum distillation to give 1.9 g of 4-chlorophenyltrimethyltin as a colorless oil (yield 64%).
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