Imidazole → 1-[3-Fluoro-4-(1H-imidazol-1-yl)phenyl]ethan-1-one

HRID 1446475Notes

Reaction equation

HRID 1446475 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH3:17][C:18]([C:20]1[CH:25]=[CH:24][C:23](F)=[C:22]([F:27])[CH:21]=1)=[O:19]>C(OCC)(=O)C.O>[F:27][C:22]1[CH:21]=[C:20]([C:18](=[O:19])[CH3:17])[CH:25]=[CH:24][C:23]=1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1230521-(3,4-Difluorophenyl)ethan-1-one

Product 1

HCID 284144171-[3-Fluoro-4-(1H-imidazol-1-yl)phenyl]ethan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Imidazole (543 mg) and potassium carbonate (1.80 g) were added to a DMF (15 mL) solution of 3,4-difluoroacetophenone (1.0 mL). After agitating reaction solution at 80° C. for 4 hours, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent:hexane:ethyl acetate=5:1→ethyl acetate), and 1.40 g of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. customreaction solution at 80° C. for 4 hours
  2. customthe organic layer was partitioned
  3. washAfter the obtained organic layer was washed with a saturated saline solution, it
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (elution solvent:hexane:ethyl acetate=5:1→ethyl acetate)

Sources & evidence

ORD record
ord-7d4b987526924365baf7f7e8bfac7777
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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