Benzyl Bromide → 1-Benzyl-2-[1-(2,3-dimethylphenyl)ethyl]-1h-imidazole

HRID 734453Notes

Reaction equation

HRID 734453 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([C:11]1[NH:12][CH:13]=[CH:14][N:15]=1)[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CC(C)=O>[CH2:22]([N:15]1[CH:14]=[CH:13][N:12]=[C:11]1[CH:9]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[CH3:1])[CH3:10])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 216625422-(1-(2,3-Dimethylphenyl)ethyl)-1H-imidazole

Product 1

HCID 247391001-Benzyl-2-[1-(2,3-dimethylphenyl)ethyl]-1h-imidazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of the compound of Example 1 (100 mg, 0.50 mmol) and caesium carbonate (407 mg, 1.25 mmol) in acetone (4 ml) was added benzyl bromide (171 mg, 1.00 mmol). The reaction mixture was stirred at room temperature, under nitrogen, for 18 h and then concentrated in vacuo. The residue was partitioned between water (10 ml) and ethyl acetate (10 ml) and the two layers were separated. The aqueous layer was extracted with ethyl acetate (10 ml) and the combined organic phases were dried (MgSO4) and concentrated in vacuo.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between water (10 ml) and ethyl acetate (10 ml)
  3. customthe two layers were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate (10 ml)
  5. dry with materialthe combined organic phases were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cbcd07f2baa248009dc46bc604c5bd70
Source dataset
uspto-grants-2009_09
Patent number
US07592362B2

Reaction notes

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