Hexane → 3,5-Dimethyl-4-trimethylsilylbromobenzene

2,6-Dimethyl-4-bromoiodobenzene (5.04 g, 16.2 mmol) was dissolved in diethyl ether (50 ml). To the solution was then added dropwise a hexane solution of n-butyl lithium (2.6 M, 6.5 ml) at −50° C. The mixture was then stirred at the same temperature for 45 minutes. To the mixture was then added dropwise trimethylsilyl trifluoromethanesulfonate (3.7 ml, 19.4 mmol). The mixture was then stirred at −30° C. for 30 minutes and at room temperature overnight. After the quenching of the reaction with water, the product was then extracted with diethyl 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 using a glass tube oven so that it was purified to obtain 3,5-dimethyl-4-trimethylsilylbromobenzene (3.54 g; yield: 85%).

1. stirringThe mixture was then stirred at −30° C. for 30 minutes and at room temperature overnight
2. customAfter the quenching of the reaction with water
3. extractionthe product was then extracted with diethyl ether
4. dry with materialThe resulting organic phase was then dried over magnesium sulfate
5. distillationThe solvent was then distilled off
6. customThe crude product thus obtained
7. distillationwas then distilled under reduced pressure
8. customwas purified

ORD record

ord-a2c939712ae74679a0a34cfd7765bb4f

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07189790B2