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

HRID 1514998Notes

Reaction equation

HRID 1514998 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.[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]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 819704-Bromo-3,5-dimethylphenol

Product 1

HCID 16128203(4-Bromo-3,5-dimethylphenoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  1. additionAfter the addition
  2. customwas recooled to 0° C.
  3. customthe reaction was quenched with water
  4. extractionThe aqueous layer was extracted with Et2O
  5. washthe organic layer was washed with water, brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e65cdc74f36447088561100d2abb57bb
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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