Imidazole → (3-Bromophenoxy)(tert-butyl)dimethylsilane

HRID 1060890Notes

Reaction equation

HRID 1060890 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 115633-BromophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11254705(3-Bromophenoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Bromophenol (7.65 g, 0.044 mol) was dissolved in anhydrous CH2Cl2 (50 mL) at room temperature and treated with imidazole (6.02 g, 0.088 mmol) and tert-butyl(dimethyl)silyl chloride (8.0 g, 0.053 mol). After stirring for 3 days, the reaction mixture was partitioned between CH2Cl2 and H2O. The aqueous layer was washed with CH2Cl2 (2×), the organics combined and dried (Na2SO4). Filtration and concentration in vacuo followed by trituration of the residue to remove the solid imidazole gave the title compound.

Workup

  1. customthe reaction mixture was partitioned between CH2Cl2 and H2O
  2. washThe aqueous layer was washed with CH2Cl2 (2×)
  3. dry with materialdried (Na2SO4)
  4. filtrationFiltration and concentration in vacuo
  5. customto remove the solid imidazole

Sources & evidence

ORD record
ord-37ed95a78a984f8c9e1432a5236136b2
Source dataset
uspto-grants-2003_02
Patent number
US06525074B2

Reaction notes

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