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

HRID 508006Notes

Reaction equation

[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.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][Si:20]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22])=[CH:4][C:3]=1[CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-bromo-3,5-dimethylphenol (25.4 g, 126.2 mmol) and imidazole (9.5 g, 138.9 mmol) in N,N-dimethylformamide (300 mL) was added tert-butyldimethylchlorosilane (20.9 g, 138.9 mmol) under stirring at 0° C., and the mixture was stirred at room temperature for 5 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=10/1) to give the title compound (38.7 g, yield 97%) as a colorless oil.

Workup

stirringthe mixture was stirred at room temperature for 5 hr
washwashed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=10/1)

Sources & evidence

ORD record: ord-ef0045fe526a418b97bb9d3c22f14059
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786165B2

Reaction notes

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