Water → 1-(3-bromophenyl)-2-[1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]ethane-1,2-dione

HRID 646232Notes

Reaction equation

HRID 646232 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[N:12][N:13]([CH2:15][C:16]([F:19])([F:18])[F:17])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])(O)=[O:21].[Na+].[O-]S([O-])(=O)=O.[Mg+2].[Mn]([O-])(=O)(=O)=O.[K+].[OH2:37]>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:21])[C:9]([C:10]2[CH:11]=[N:12][N:13]([CH2:15][C:16]([F:17])([F:18])[F:19])[CH:14]=2)=[O:37])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 597727304-[(3-bromophenyl)ethynyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazole

Product 1

HCID 597726911-(3-bromophenyl)-2-[1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]ethane-1,2-dioneYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-[(3-bromophenyl)ethynyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazole (4.90 g, 14.9 mmol) in acetone (150 mL) is added a warm (˜40° C.) solution of NaHCO3 (0.75 g, 8.9 mmol) and MgSO4 (2.70 g, 22.4 mmol) in H2O (150 mL) followed by the addition of solid potassium permanganate (5.2 g, 32.8 mmol) in one portion. After stirring for 40 minutes at room temperature, the reaction mixture is extracted with a solution of Et2O/hexane (1/1) until no product left in aqueous layer. The combined organic extracts is dried (MgSO4) and concentrated to dryness to afford the title compound (4.4 g, 82%) as a solid. mp: 66-67° C. MS (−) ES: 359 (M−H)−.

Workup

  1. extractionthe reaction mixture is extracted with a solution of Et2O/hexane (1/1) until no product
  2. waitleft in aqueous layer
  3. dry with materialThe combined organic extracts is dried (MgSO4)
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-05190f0c846c4fe6be16edb35008c42f
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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