Hexane → 3-Chloro-4-trimethylsilyl-bromobenzene

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Reaction Steps

3-chloro-4-iodobromobenzene (3.1 g) was dissolved in diethyl ether (100 ml). To the solution was then added dropwise a hexane solution of n-butyl lithium (1.59 M, 6.1 ml) at −78° C. The mixture was then stirred at the same temperature for 30 minutes. To the mixture was then added dropwise trimethylsilyl trifluoromethane sulfonate (3.77 ml; 17.4 mmol). The mixture was then stirred for 1 hour. After the quenching of the reaction by gradually adding water over an ice bath, the product was then extracted with ether. The resulting organic phase was then dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. The crude product thus obtained was then purified twice through silica gel column chromatography (silica gel produced by Merck Ltd., Japan; hexane) to obtain 3-chloro-4-trimethylsilyl-bromobenzene (2.3 g) (yield: 90%).

Provenance & Evidence