2-Fluorobenzoyl chloride → 2-[1-(2-Fluorobenzoyl)-4,5-dimethyl-1H-imidazol-2-yl]-1-(2-fluorophenyl)ethenyl 2-fluorobenzoate

HRID 1610825Notes

Reaction equation

HRID 1610825 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1.[F:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13]>C(#N)C>[F:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([O:13][C:12]([C:11]1[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=1[F:9])=[CH:1][C:2]1[N:3]([C:12](=[O:13])[C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[F:9])[C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1)=[O:13]

Participants

4

Reactant 2

HCID 98082-Fluorobenzoyl chlorideHCID 699762,4,5-Trimethylimidazole

Product 1

HCID 695894172-[1-(2-Fluorobenzoyl)-4,5-dimethyl-1H-imidazol-2-yl]-1-(2-fluorophenyl)ethenyl 2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

3.00 g (27.23 mmol) 2,4,5-trimethyl-1H-imidazol and 9.37 g (92.59 mmol) TEA are dissolved in 50 ml acetonitrile and cooled to 0° C. 14.25 g (89.87 mmol) 2-fluoro-benzoylchloride are added dropwise and the mixture is stirred 2 h at RT and let stand overnight. The solvent is removed under vacuum, the residue is dissolved in toluene and washed twice with water. The organic phase is filtered through Tonsil (K60) and concentrated under vacuum. The product is used without further purification.

Workup

  1. waitlet stand overnight
  2. customThe solvent is removed under vacuum
  3. dissolutionthe residue is dissolved in toluene
  4. washwashed twice with water
  5. filtrationThe organic phase is filtered through Tonsil (K60)
  6. concentrationconcentrated under vacuum
  7. customThe product is used without further purification

Sources & evidence

ORD record
ord-f1169e002d6341e795cbecafdb26e692
Source dataset
uspto-grants-2006_01
Patent number
US06984646B2

Reaction notes

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