Imidazole → (4-Bromo-3,5-dimethylphenoxy)(tert-butyl)dimethylsilane

Reaktionsgleichung

[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].N1C=CN=C1.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][Si:20]([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21])=[CH:4][C:3]=1[CH3:10]

Komponenten

Versuchsvorschrift

A solution of 4-bromo-3,5-dimethylphenol (2.1 g, 10 mmol) and imidazole (1.50 g, 22 mmol) in DMF (15 mL) was cooled to 0° C. then TBDMSCl (1.66 g, 11 mmol) was added. After the addition, the solution was warmed up to ambient temperature and was stirred for 10 min. The solution was recooled to 0° C. and the reaction was quenched with water. The aqueous layer was extracted with Et2O and the organic layer was washed with water, brine, dried with MgSO4 and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (10:1) to give (4-bromo-3,5-dimethylphenoxy)-tert-butyl-dimethylsilane as a pale yellow solid.