1-(4-Bromophenyl)-4,4,4-trifluorobutane-1,3-dione → 5-(4-bromophenyl)-1-[3-fluoro-4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole

HRID 396775Notes

Reaction equation

HRID 396775 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([NH:13][NH2:14])[CH:6]=[CH:7][C:8]=1[S:9]([CH3:12])(=[O:11])=[O:10].[F:15][C:16]([F:30])([F:29])[C:17](=O)[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=1)=O>CCO>[Br:27][C:24]1[CH:23]=[CH:22][C:21]([C:19]2[N:13]([C:5]3[CH:6]=[CH:7][C:8]([S:9]([CH3:12])(=[O:10])=[O:11])=[C:3]([F:2])[CH:4]=3)[N:14]=[C:17]([C:16]([F:15])([F:29])[F:30])[CH:18]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 27714771-(4-Bromophenyl)-4,4,4-trifluorobutane-1,3-dioneHCID 22316658[3-Fluoro-4-(methylsulfonyl)phenyl]hydrazine hydrochloride

Product 1

HCID 223167185-(4-bromophenyl)-1-[3-fluoro-4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazoleYield 86.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[3-fluoro-4-(methylsulfonyl)phenyl]hydrazine hydrochloride (0.354 g, 1.47 mmol) was added to a solution of 4,4,4-Trifluoro-1-(4-bromophenyl)butane-1,3-dione (0.395 g, 1.34 mmol) in EtOH (20 mL). The mixture was heated at reflux temperature for 17 hours and cooled down to room temperature. The reaction mixture was concentrated in vacuo, and the residue was taken up in ethyl acetate, washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (3/1). The resulting solid was recrystallized from ethyl acetate/hexane to give the subtitle compound (0.537 g, 86.6% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 17 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with hexane/ethyl acetate (3/1)
  9. customThe resulting solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-52d886c3c79848138fc2c244c12c65ba
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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