Imidazole → 1-(4-iodobenzyl)-1H-imidazole

HRID 2092393Notes

Reaction equation

HRID 2092393 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([O-])([O-])=O.[K+].[K+].[I:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1.O>CN(C=O)C>[I:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 11430Potassium CarbonateHCID 9542584-Iodobenzyl bromide

Product 1

HCID 159840721-(4-iodobenzyl)-1H-imidazoleYield 45.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of imidazole (400 mg, 5.88 mmol) and K2CO3 (1.22 g, 8.81 mmol) in DMF (19 ml) was added 4-iodobenzyl bromide (1.83 g, 6.17 mol) at RT under protection from light. After stirring for 11.5 h, the reaction mixture was poured into water. The aqueous layer was extracted twice with EtOAc, the combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to afford the title compound (757 mg, 2.66 mmol, 45%) as a beige solid. HPLC: EtRet=3.838 min; LC-MS: m/z 285.2 [M+H]+.

Workup

  1. extractionThe aqueous layer was extracted twice with EtOAc
  2. washthe combined organic layers were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9fa050c5512345fdb1917b64b6ba9ea8
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

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