2,4,5-Tribromoimidazole → 2,4,5-tribromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-Imidazole

HRID 1627230Notes

Reaction equation

HRID 1627230 reaction equation
[Br:1][C:2]1[NH:3][C:4]([Br:8])=[C:5]([Br:7])[N:6]=1.[H-].[Na+].[CH3:11][Si:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][O:15][CH2:16]Cl>CN(C)C=O.O>[Br:1][C:2]1[N:3]([CH2:16][O:15][CH2:14][CH2:13][Si:12]([CH3:19])([CH3:18])[CH3:11])[C:4]([Br:8])=[C:5]([Br:7])[N:6]=1

Participants

6

Reactant 3

HCID 162532,4,5-TribromoimidazoleHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 109062032,4,5-tribromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-Imidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4,5-tribromo-1H-imidazole (10.3 g, 32 8 mmol) in anhydrous N,N-dimethylformamide (100 ml) is slowly added NaH (1.4 g, 36.1 mmol, 60% in mineral oil) at room temperature. The suspension is stirred for 15 minutes and 2-(Trimethylsilyl)ethoxymethyl chloride (5.8 ml, 32.8 mmol) is added. The mixture is stirred at room temperature for 3 hours. The reaction mixture is diluted with water (250 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layer is washed with water (50 ml), brine, dried over MgSO4, filtered, and concentrated in vacuo to yield 2,4,5-tribromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole as a yellow waxy solid 13.8 g, 97%.

Workup

  1. customat room temperature
  2. stirringThe mixture is stirred at room temperature for 3 hours
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washThe combined organic layer is washed with water (50 ml), brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ccaf9c5ec2d94a3380f7340e68d3c6d6
Source dataset
uspto-grants-2014_07
Patent number
US08785489B2

Reaction notes

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