Ethyl Acetate → 2-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole

HRID 500797Notes

Reaction equation

HRID 500797 reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.N#C[Br:16].CCOC(C)=O>C(#N)C>[Br:16][C:8]1[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:13])([CH3:12])[CH3:1])[CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10476Cyanogen BromideHCID 110526051-((2-(Trimethylsilyl)ethoxy)methyl)-1H-imidazole

Product 1

HCID 594245422-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazoleYield 32.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 107 (100 mg, 0.50 mmol) in acetonitrile (1 mL) at room temperature was added cyanogen bromide (107 mg, 1.0 mmol) and the mixture was allowed to stir at room temperature for 3 h, concentrated to dryness and partitioned between EtOAc and water. The organic phase was collected, dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified by column chromatography (eluents EtOAc/hexane 25:75, then EtOAc), to afford the title compound 108 (45 mg, 32% yield) as a colorless oil. MS (m/z) 277.0/279.0 (M+H).

Workup

  1. concentrationconcentrated to dryness
  2. custompartitioned between EtOAc and water
  3. customThe organic phase was collected
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography (eluents EtOAc/hexane 25:75

Sources & evidence

ORD record
ord-645191db71334b60b77f31bf9d24e894
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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