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

HRID 1056457Notes

Reaction equation

HRID 1056457 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-e87b9dd7f005412fa6c8a5d398941aaa
Source dataset
uspto-grants-2016_07
Patent number
US09398767B2

Reaction notes

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