Imidazole → (4-Bromo-3-isopropyl-phenoxy)-tert-butyl-dimethyl-silane

HRID 1861489Notes

Reaction equation

HRID 1861489 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH:9]([CH3:11])[CH3:10].Cl[Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])=[CH:4][C:3]=1[CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 225688014-Bromo-3-isopropylphenol2×

Product 1

HCID 22568908(4-Bromo-3-isopropyl-phenoxy)-tert-butyl-dimethyl-silaneYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromo-3-isopropyl-phenol (Intermediate 144, 1.13 g, 5.25 mmols), chloro-tert-butyl-dimethylsilane (0.95 g, 6.30 mmols), and imidazole (428.0 mg, 6.3 mmols) in 10 mL DMF was stirred at 25° C. for 3 hours. The solution was diluted with H2O and extracted with Et2O and the combined organic layers were washed with H2O, saturated aqueous NaCl, and dried (MgSO4) before being concentrated under reduced pressure. Column chromatography (1-2% EtOAc-hexanes) afforded 1.50 g (87%) of the title compound as a colorless oil.

Workup

  1. extractionextracted with Et2O
  2. washthe combined organic layers were washed with H2O, saturated aqueous NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationbefore being concentrated under reduced pressure

Sources & evidence

ORD record
ord-3def24b459da41a88b368cfade160ae4
Source dataset
uspto-grants-2003_03
Patent number
US06531599B2

Reaction notes

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