5-Bromo-2-ethyl-1H-imidazole-4-methanol → HCID 10058687, compound

HRID 1828817Notes

Reaction equation

HRID 1828817 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH2:9][CH3:10])[NH:5][C:6]=1[CH2:7][OH:8]>CN(C)C=O.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[NH:3][C:4]([CH2:9][CH3:10])=[N:5][C:6]=1[CH:7]=[O:8]

Participants

4

Reactant 1

HCID 102420335-Bromo-2-ethyl-1H-imidazole-4-methanol

Product 1

HCID 10058687HCID 10058687, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

4-Bromo-2-ethyl-5-(hydroxymethyl)imidazole (18.9 g) was dissolved in dry dimethylformamide (189 ml), and manganese dioxide (80.1 g) was added. The mixture was stirred at room temperature for 5 hr and left standing overnight. The reaction mixture was filtered through celite and insoluble matter was washed with chloroform. The filtrate and washing were combined and concentrated to dryness under reduced pressure. The residue was washed with water to give 5-bromo-2-ethylimidazole-4-carbaldehyde (12.9 g) as a brown powder.

Workup

  1. waitleft
  2. waitstanding overnight
  3. filtrationThe reaction mixture was filtered through celite and insoluble matter
  4. washwas washed with chloroform
  5. washThe filtrate and washing
  6. concentrationconcentrated to dryness under reduced pressure
  7. washThe residue was washed with water

Sources & evidence

ORD record
ord-a43b97025035486fb144d0c326a121fc
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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