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

HRID 2287075Notes

Reaction equation

HRID 2287075 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.Br[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]Br.CN(C)C=O>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[CH3:1])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 77304-BromoanisoleHCID 11430Potassium CarbonateHCID 127492-Methylimidazole

Product 1

HCID 127971081-(4-methoxyphenyl)-2-methyl-1H-imidazoleYield 41%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 16.4 parts of 2-methyl-1H-imidazole, 37.4 parts of 1-bromo-4-methoxybenzene, 1 part of copper(I)bromide, 20 parts of potassium carbonate and 270 parts of N,N-dimethylformamide is stirred and refluxed for one week. The reaction mixtuure is cooled, poured onto water and the whole is extracted with 2,2'-oxybispropane. The extract is washed twice with a diluted hydrochloric acid solution. The acid aqueous phase is separated and alkalized with sodium hydroxide. The product is extracted twice with 2,2'-oxybispropane. The combined extracts are dried, filtered and evaporated, yielding 4 parts (41%) of 1-(4-methoxyphenyl)-2-methyl-1H-imidazole as a residue.

Workup

  1. temperaturerefluxed for one week
  2. temperatureThe reaction mixtuure is cooled
  3. additionpoured onto water
  4. extractionthe whole is extracted with 2,2'-oxybispropane
  5. washThe extract is washed twice with a diluted hydrochloric acid solution
  6. customThe acid aqueous phase is separated
  7. extractionThe product is extracted twice with 2,2'-oxybispropane
  8. customThe combined extracts are dried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-4c7df54075f347c6b7531cdb7c8b644b
Source dataset
uspto-grants-1981_05
Patent number
US04268680

Reaction notes

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