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

HRID 1583048Notes

Reaction equation

HRID 1583048 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[C:14]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])([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:18]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:20])[CH3:19]

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 6344DichloromethaneSolvent2×

Procedure

A suspension of 3-bromo-phenol (5.5 g, 31.8 mmoles), imidazole (4.3 g, 63.6 mmoles) in CH2Cl2 (70 ml) was added dropwise to a solution of tert-butyl-chloro-dimethylsilane (5.3 g, 35 mmoles) in CH2Cl2 (5 ml) at 0° C. The reaction mixture was stirred for 3 hours at room temperature then evaporated to dryness under vacuum. The residue was partitioned between water and ethyl acetate and from the organic solution after essiccation over MgSO4, filtration and evaporation the title compound was obtained.

Workup

  1. customthen evaporated to dryness under vacuum
  2. customThe residue was partitioned between water and ethyl acetate and from the organic solution after essiccation
  3. filtrationover MgSO4, filtration and evaporation the title compound
  4. customwas obtained

Sources & evidence

ORD record
ord-cac01fba78e840d5ba4e11bb0a776a5b
Source dataset
uspto-grants-2004_05
Patent number
US06740712B2

Reaction notes

Loading…