8-Hydroxyquinoline → 4-Hydroxymethyl 1-(4-iodophenyl)imidazole

HRID 642994Notes

Reaction equation

HRID 642994 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][CH:3]=1.[OH:9][CH2:10][C:11]1[N:12]=[CH:13][NH:14][CH:15]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I.CCOC(C)=O.O>[I:8][C:5]1[CH:6]=[CH:7][C:2]([N:14]2[CH:15]=[C:11]([CH2:10][OH:9])[N:12]=[CH:13]2)=[CH:3][CH:4]=1

Participants

9

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 12208p-DiiodobenzeneHCID 178519868HCID 178519868, compound

Product 1

HCID 592601064-Hydroxymethyl 1-(4-iodophenyl)imidazoleYield 22.3%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 1,4-diiodobenzene 9.1 (4.00 g, 12.1 mmol), 4-(hydroxymethyl)imidazole 9.2 (1.20 g, 12.2 mmol), 8-hydroxyquinoline (0.176 g, 1.21 mmol) and K2CO3 (1.69 g, 12.2 mmol) in DMSO (12 mL) was degassed before being charged with CuI (0.230 g, 1.21 mmol). The mixture in a sealed tube was heated at 130° C. overnight. Water and EtOAc were added. The mixture was filtered. The organic layer was separated, then applied to a silica gel column, which was eluted with 0-5% MeOH in CH2Cl2 to give (1-(4-iodophenyl)-1H-imidazol-4-yl)methanol 9.3 (0.810 g) and its isomer (1-(4-iodophenyl)-1H-imidazol-5-yl)methanol 9.4. MS 301.2 (M+H).

Workup

  1. customwas degassed
  2. filtrationThe mixture was filtered
  3. customThe organic layer was separated
  4. washwas eluted with 0-5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-cfd0932a1d1e4888b8f732bc645af0e7
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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