Ethyl Acetate → 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxylic acid

HRID 1618921Notes

Reaction equation

HRID 1618921 reaction equation
I(O)(=O)(=O)=O.[F:6][C:7]1[N:11]([CH3:12])[N:10]=[C:9]([CH:13]([F:15])[F:14])[C:8]=1[CH:16]=[O:17].[Cr](Cl)([O-])(=O)=[O:19].[NH+]1C=CC=CC=1.C(OCC)(=O)C>C(#N)C>[F:6][C:7]1[N:11]([CH3:12])[N:10]=[C:9]([CH:13]([F:14])[F:15])[C:8]=1[C:16]([OH:19])=[O:17]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 65185Metaperiodic acidHCID 19754735HCID 19754735, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 231925843-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A suspension of 79.7 g (350 mmol) of periodic acid in 640 ml absolute acetonitrile was stirred for 30 min. To this was added 56.6 g (318 mmol) of 5-fluoro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde at 0° C. and a solution of 1.4 g (6 mmol) of pyridinium chlorochromate in 130 ml dry acetonitrile. The reaction mixture was stirred for 2.5 hours at room temperature. 1600 ml of ethyl acetate was added to the reaction mixture and the separated organic phase was washed consecutively with brine/water(1:1), saturated sodium metabisulfite and brine. Then the organic phase was dried with sodium sulphate, and evaporated under vacuum to give the expected product as a pale yellow solid.

Workup

  1. stirringThe reaction mixture was stirred for 2.5 hours at room temperature
  2. washthe separated organic phase was washed consecutively with brine/water(1:1), saturated sodium metabisulfite and brine
  3. dry with materialThen the organic phase was dried with sodium sulphate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-0b69409ee8fd487e9cce594cf9a67802
Source dataset
uspto-grants-2014_07
Patent number
US08772266B2

Reaction notes

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