Imidazole → 1-Bromo-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-benzene

HRID 1254268Notes

Reaction equation

HRID 1254268 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 72442-BromophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 112199121-Bromo-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-benzeneYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromophenol (5 mL, 47 mmol), imidazole (8 g, 118 mmol) and tert-butyldimethylsilyl chloride (8.6 g, 57 mmol) in DMF (50 mL) was stirred at rt overnight. The reaction was treated with water (150 mL) and extracted with Et2O (4×25 mL). The organic phase was washed with 50% aq lithium chloride solution twice, dried over MgSO4 and filtered. The solvent was evaporated and the crude product was purified by filtration through silica gel, washing with 1:1 EtOAc/hexanes to afford bromo-2-[(tert-butyl)dimethylsiloxy]benzene (13.4 g, 99%).

Workup

  1. extractionextracted with Et2O (4×25 mL)
  2. washThe organic phase was washed with 50% aq lithium chloride solution twice
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. filtrationthe crude product was purified by filtration through silica gel
  7. washwashing with 1:1 EtOAc/hexanes

Sources & evidence

ORD record
ord-e1ac997f8a3145d5930a5ad85e4a57c9
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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