Methyl iodide → 4-(4-Bromophenyl)-1-methyl-1H-imidazole

HRID 1183199Notes

Reaction equation

HRID 1183199 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][NH:11][CH:12]=2)=[CH:4][CH:3]=1.IC.[C:15](=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][N:11]([CH3:15])[CH:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 178419352HCID 178419352, compound

Product 1

HCID 532492914-(4-Bromophenyl)-1-methyl-1H-imidazoleYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Step 1 product (3.1 g, 13.90 mmol) in 50 mL of THF was added iodomethane (1.74 mL, 27.8 mmol) and cesium carbonate (5.43 g, 16.68 mmol). The reaction was stirred at rt overnight. EtOAc (150 mL) was added to the reaction, and the mixture was washed with water (2 times) and brine, dried over MgSO4, and concentrated to dryness. The residue was purified by silica column (10-80% EtOAc in hexanes) to give 2.8 g (yield 85%) 4-(4-bromophenyl)-1-methyl-1H-imidazole. LCMS: [M+1]+=237.

Workup

  1. washthe mixture was washed with water (2 times) and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by silica column (10-80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-44a9247b76874846b8c3c10dc2ebc5ac
Source dataset
uspto-grants-2014_03
Patent number
US08664253B2

Reaction notes

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