Imidazole → 4-Bromo-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-methoxybenzene

HRID 1375977Notes

Reaction equation

HRID 1375977 reaction equation
N1C=CN=C1.[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:23][CH3:24])=[C:19]([CH:22]=1)[CH2:20][OH:21].O>CN(C=O)C>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:23][CH3:24])=[C:19]([CH:22]=1)[CH2:20][O:21][Si:10]([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 6122985-Bromo-2-methoxybenzyl alcohol

Product 1

HCID 120384334-Bromo-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-methoxybenzeneYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (3.45 g) and t-butyldimethylchlorosilane (17.6 g) were added to a solution of 5-bromo-2-methoxybenzyl alcohol (10.0 g) in DMF (100 ml) under cooling with ice and the mixture was stirred for two hours. The reaction mixture was added to ice-cooled water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain [(5-bromo-2-methoxybenzyl)oxy](t-butyl)dimethylsilane (15.2 g).

Workup

  1. temperatureunder cooling with ice
  2. additionThe reaction mixture was added to ice-
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1695856f7ede479dbd469d50171e3729
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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