Benzyl Bromide → 1-Benzyl-5-formyl-2-methylimidazole

HRID 1064325Notes

Reaction equation

HRID 1064325 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9]([C:11]1[N:12]=[C:13]([CH3:16])[NH:14][CH:15]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([N:12]1[C:11]([CH:9]=[O:10])=[CH:15][N:14]=[C:13]1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178418999HCID 178418999, compound

Product 1

HCID 3043301-Benzyl-5-formyl-2-methylimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (21.4 ml, 0.18 mol) was added carefully to a mixture of 4-formyl-2-methylimidazole (18.1 g, 0.16 mol) and potassium carbonate (45.0 g, 0.33 mol) in DMF (100 ml) at 0° C. and the reaction mixture allowed to warm to ambient temperature. The mixture was then partitioned between EtOAc and saturated aqueous sodium hydrogen carbonate solution, the organic phase separated and dried. The volatiles were removed by evaporation to give the title compound as crude mixture of regioisomers 32.0 g, (99%). M/z: 201.

Workup

  1. customThe mixture was then partitioned between EtOAc and saturated aqueous sodium hydrogen carbonate solution
  2. customthe organic phase separated
  3. customdried
  4. customThe volatiles were removed by evaporation

Sources & evidence

ORD record
ord-e37d914dbdf44fd98fb691777fdbea2d
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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