Dichloromethane → (4-bromo-2-methyl-1H-imidazol-5-yl)methanol

HRID 342150Notes

Reaction equation

HRID 342150 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH3:9])[NH:5][C:6]=1[CH2:7][OH:8].C(Cl)Cl>[O-2].[O-2].[Mn+4].O1CCOCC1>[Br:1][C:2]1[N:3]=[C:4]([CH3:9])[NH:5][C:6]=1[CH2:7][OH:8].[Br:1][C:2]1[N:3]=[C:4]([CH3:9])[NH:5][C:6]=1[CH:7]=[O:8]

Participants

6

Reactant 2

HCID 6344DichloromethaneHCID 22625922(4-bromo-2-methyl-1H-imidazol-5-yl)methanol

Product 2

HCID 22625922(4-bromo-2-methyl-1H-imidazol-5-yl)methanolHCID 178432447HCID 178432447, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

4-Bromo-5-hydroxymethyl-2-methylimidazole was prepared according to the procedure described by S. P. Watson, Synthetic Communications, 22, 2971-2977 (1992). A solution of 4-bromo-5-hydroxymethyl-2-methylimidazole (4.18 g, 21.9 mmol) was refluxed with manganese dioxide (16.1 g) in 1:1 methylene chloride:dioxane (200 mL) for 16 h. The cooled reaction was filtered through celite and concentrated to yield the title compound as a pale yellow solid. 1H NMR (CDCl3, 300 MHz) δ 9.57 (1H, s), 2.52 (3H, s).

Workup

  1. customThe cooled reaction
  2. filtrationwas filtered through celite and
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fcf2586269d24125846407fb4130ddf4
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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