4'-Fluoroacetophenone → 1-[4-(4-Methyl-1H-imidazol-1-yl)phenyl]ethan-1-one

HRID 1460293Notes

Reaction equation

HRID 1460293 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][C:12]1[N:13]=[CH:14][NH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][C:12]1[N:13]=[CH:14][N:15]([C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 178418800HCID 178418800, compound

Product 1

HCID 150053821-[4-(4-Methyl-1H-imidazol-1-yl)phenyl]ethan-1-oneYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4'-fluoroacetophenone (13.8 g, 100 mmol), 4-methylimidazole (8.2 g, 100 ml) and potassium carbonate (20.7 g, 150 mmol) in dry dimethylformamide (190 ml) was heated at 150° C. for 23 hours. Most of the solvent was evaporated at reduced pressure and the residue was partitioned between ethyl acetate and brine. The organic layer was washed (3×) with brine, dried (magnesium sulphate) and evaporated to leave a sticky solid which was purified by flash chromatography (eluting 5% diethylamine in ethylacetate). Recrystallization from ethyl acetate/hexane afforded the title compound (yield 4 g, 20%), m.p. 100° C.

Workup

  1. customMost of the solvent was evaporated at reduced pressure
  2. customthe residue was partitioned between ethyl acetate and brine
  3. washThe organic layer was washed (3×) with brine
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated
  6. customto leave a sticky solid which
  7. customwas purified by flash chromatography (eluting 5% diethylamine in ethylacetate)
  8. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2f2e37604dae482cbd1e777a47a3c67a
Source dataset
uspto-grants-1991_12
Patent number
US05070205

Reaction notes

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