Imidazole → (4-Bromo-3,5-dimethyl-phenoxy)triisopropylsilane

HRID 1836552Notes

Reaction equation

HRID 1836552 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.Cl[Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH:18]([Si:17]([O:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([Br:1])=[C:3]([CH3:10])[CH:4]=1)([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 819704-Bromo-3,5-dimethylphenolHCID 139400Triisopropylsilyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 22605990(4-Bromo-3,5-dimethyl-phenoxy)triisopropylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, 5.0 g (24.87 mmol) of 4-bromo-3,5-dimethylphenol, 2.03 g (29.84 mmol) of imidazole and 6.23 g (32.33 mmol) of chloro(triisopropyl)silane are stirred in 20 ml of dimethylformamide overnight. Saturated sodium bicarbonate solution is then added, and the mixture is extracted three times with diethyl ether. The combined organic phases are washed with water and dried with sodium sulphate, and the solvent is removed under reduced pressure. This gives 7.5 g (84% of theory) of 4-bromo-3,5-dimethylphenyl triisopropylsilyl ether.

Workup

  1. extractionthe mixture is extracted three times with diethyl ether
  2. washThe combined organic phases are washed with water
  3. dry with materialdried with sodium sulphate
  4. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-78546b7ae1c04eed9ecea846cf16bd32
Source dataset
uspto-grants-2004_08
Patent number
US06777442B2

Reaction notes

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