Iodine → 4-(Imidazol-1-yl)-2-iodophenol

HRID 228695

Reaction equation

HRID 228695 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[I:13]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>O.CO.ClCCl>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([I:13])[CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 3

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 823151-(p-Hydroxyphenyl)imidazole

Product 1

HCID 222744934-(Imidazol-1-yl)-2-iodophenolYield 14%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-(Imidazol-1-yl)phenol (500 mg) was dissolved in water (6 ml), methanol (18 ml), and dichloromethane (6 ml) to prepare a solution. Iodine (1.58 g) was added to the solution, and the mixture was stirred at room temperature for 8 days. An aqueous sodium thiosulfate solution and methanol were added to the reaction solution, and the mixture was stirred and was then concentrated. The concentrate was extracted with chloroform, and the chloroform layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give 4-(imidazol-1-yl)-2-iodophenol (123 mg, yield 14%).

Workup

  1. stirringthe mixture was stirred
  2. concentrationwas then concentrated
  3. extractionThe concentrate was extracted with chloroform
  4. washthe chloroform layer was then washed with water and saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. distillationby distillation under the reduced pressure
  8. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-6443b95ed90b4833a2ab64a8d940ff33
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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