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

HRID 1374128Notes

Reaction equation

HRID 1374128 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-a0744d42dd234db5b864520a01a750ea
Source dataset
uspto-grants-2007_01
Patent number
US07164018B2

Reaction notes

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