Imidazole → (4-Bromophenoxy)(tert-butyl)dimethylsilane

HRID 863858Notes

Reaction equation

HRID 863858 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=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:7]=[CH:6][C:5]([O:8][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 78084-BromophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 4227167(4-Bromophenoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-bromophenol (5.1 g; 29 mmol) and imidazole (2 g; 29 mmol) in CH2Cl2 (50 ml) at 0° C. is added t-butyldimethylsilyl chloride (4.4 g; 29 mmol) and the reaction is stirred for 15 hours. This is then diluted with CH2Cl2, washed with H2O, ammonium chloride solution, NaHCO3, dried (MgSO4) and concentrated in vacuo to yield 4-bromo-t-butyldimethylsilyloxybenzene as an oil which is used directly in Step B without further purification.

Workup

  1. washwashed with H2O, ammonium chloride solution, NaHCO3
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33fb72acb2da405688ec73dbefb9d70b
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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