4-Bromoanisole → 1-(4-methoxyphenyl)-2-phenyl-1H-imidazole

HRID 224443

Reaction equation

HRID 224443 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([N:11]2[CH:10]=[CH:9][N:8]=[C:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 77304-BromoanisoleHCID 11430Potassium CarbonateHCID 695912-Phenylimidazole

Product 1

HCID 234610061-(4-methoxyphenyl)-2-phenyl-1H-imidazoleYield 25%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 28.8 parts of 2-phenyl-1H-imidazole, 37.4 parts of 1-bromo-4-methoxybenzene, 20 parts of potassium carbonate and 180 parts of N,N-dimethylacetamide is stirred for one week at reflux temperature. The reaction mixture is cooled, poured onto water and the product is extracted twice with 2,2'-oxybispropane. The combined extracts are dried, filtered and evaporated, yielding 10 parts (25%) of 1-(4-methoxyphenyl)-2-phenyl-1H-imidazole as a residue.

Workup

  1. temperatureat reflux temperature
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. extractionthe product is extracted twice with 2,2'-oxybispropane
  5. customThe combined extracts are dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-58e5617ee1b94187b589f0e28eefec48
Source dataset
uspto-grants-1980_11
Patent number
US04232034

Linked notes

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