Sodium Hydroxide → 3-(difluoromethyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

HRID 1843099Notes

Reaction equation

HRID 1843099 reaction equation
[F:1][CH:2]([F:18])[C:3]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([C:12]([O:14]CC)=[O:13])[N:5]([CH3:17])[N:4]=1.[OH-].[Na+]>CO>[F:18][CH:2]([F:1])[C:3]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([C:12]([OH:14])=[O:13])[N:5]([CH3:17])[N:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58542505ethyl 3-(difluoromethyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate

Product 1

HCID 585425153-(difluoromethyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 600 mg (2.20 mmol) of ethyl 3-(difluoromethyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate in 10 ml of methanol is admixed with 331 mg (3.31 mmol) of 40% strength sodium hydroxide solution and stirred for three hours at room temperature. The reaction mixture is concentrated by evaporation, admixed with water and extracted with diethyl ether. The aqueous phase is acidified with dilute hydrochloric acid and extracted twice with diethyl acetate. The organic phase is dried over sodium sulphate and, after filtration, is concentrated by evaporation. This gives 452 mg of 3-(difluoromethyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (84%).

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. extractionextracted with diethyl ether
  3. extractionextracted twice with diethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. filtrationafter filtration
  6. concentrationis concentrated by evaporation

Sources & evidence

ORD record
ord-0530905ea7ba48208bdf4179b7a4ffeb
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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