5-fluoro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde → 5-Fluoro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

HRID 1588785Notes

Reaction equation

HRID 1588785 reaction equation
[CH3:1][N:2]1[C:6]([F:7])=[C:5]([CH:8]=[O:9])[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1.O.O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:17].[K+].[K+]>CC(C)=O.O.S(=O)(=O)(O)O>[CH3:1][N:2]1[C:6]([F:7])=[C:5]([C:8]([OH:17])=[O:9])[C:4]([C:10]([F:13])([F:11])[F:12])=[N:3]1

Participants

6

Reactant 2

HCID 197547475-fluoro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehydeHCID 22102070HCID 22102070, compound

Product 1

HCID 233617235-Fluoro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acidYield 200.2%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1-methyl-3-trifluoromethyl-5-fluoro-pyrazole-4-carboxaldehyde (9.8 g) in acetone (60 mL) was stirred rapidly at RT while a solution of potassium dichromate dihydrate (5.6 g) in water (38 mL) and sulfuric acid (4.6 mL) was added. The mixture was stirred rapidly overnight then diluted with water (150 mL). The mixture was extracted with CH2Cl2 (6 ×75 mL). The combined organic solution was washed with water, dried (MgSO4), filtered and concentrated in vacuo leaving a light yellow solid (7.2 g). The solid was recrystallized from EtOAc/hexane to give the desired compound as white crystals (3.8 g). m.p. 165-166° C.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with CH2Cl2 (6 ×75 mL)
  3. washThe combined organic solution was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff25a12342044abcbbfc3978789ebd45
Source dataset
uspto-grants-1993_06
Patent number
US05223526

Reaction notes

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