Imidazole → 3-(1H-Imidazol-1-yl)benzenemethanol

HRID 2242360Notes

Reaction equation

HRID 2242360 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.C(=O)([O-])[O-].[K+].[K+].[F-].[K+]>CN(C=O)C.[Cu]>[N:10]1([C:2]2[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][CH:9]=2)[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 423003-Iodobenzyl alcoholHCID 522689Potassium Fluoride

Product 1

HCID 197444983-(1H-Imidazol-1-yl)benzenemethanolYield 86.7%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

3-Iodobenzylalcohol (5.17 g, 21.0 mmol), imidazole (1.73 g, 25.2 mmol), potassium carbonate (3.78 g, 27.3 mmol), copper (0) powder (275 mg, 4.33 mmol) and potassium fluoride (260 mg, 4.44 mmol) in DMF (30 ml) were refluxed at 175° C. for 6 h. The reaction was filtered, the solid washed with DCM and washing and filtrate concentrated. Purification by silica chromatography using DCM followed by DCM:MeOH (15:1 then 10:1) yielded (3-imidazol-1-yl-phenyl)-methanol as an orange oil (3.17 g, 72%).

Workup

  1. filtrationThe reaction was filtered
  2. washthe solid washed with DCM
  3. washwashing
  4. concentrationfiltrate concentrated
  5. customPurification by silica chromatography

Sources & evidence

ORD record
ord-39a53722e6264b1cbe7615305a149641
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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