Hexane → (4-Bromo-2,6-dichlorophenyl)(trimethyl)silane

Participants

Reaction Steps

The 2,6-Dichloro-4-bromoiodobenzene (4.48 g, 12.7 mmol) was dissolved in diethyl ether (50 ml). To the solution was then added dropwise a hexane solution of n-butyl lithium (1.56 M, 8.2 ml) at −78° C. At the same temperature, the mixture was then stirred for 1 hour. To the mixture was then added dropwise trimethylsilyl trifluoromethanesulfonate (3.2 ml, 16.5 mmol). The mixture was then stirred at −78° C. for 1 hour and at room temperature for 30 minutes. After the quenching of the reaction with water, the mixture was then extracted with ether. The resulting organic phase was then dried over magnesium sulfate. The solvent was then distilled off. The crude product thus obtained was then distilled under reduced pressure in a glass tube oven so that it was purified to obtain 3,5-dichloro-4-trimethylsilyl-bromobenzene (3.39 g; yield: 90%).

Provenance & Evidence