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

HRID 1261236Notes

Reaction equation

HRID 1261236 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-59e14e8351174a33aa7597e5b3cbb17a
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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