Water → HCID 19754735, compound

HRID 1618083Notes

Reaction equation

HRID 1618083 reaction equation
[F-:1].[K+].Cl[C:4]1[N:8]([CH3:9])[N:7]=[C:6]([CH:10]([F:12])[F:11])[C:5]=1[CH:13]=[O:14].O>CN(C=O)C>[F:1][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([CH:10]([F:12])[F:11])[C:5]=1[CH:13]=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 522689Potassium FluorideHCID 197546925-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 19754735HCID 19754735, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

96.3 g (1660 mmol) of spray-dried potassium fluoride were carefully dried under high vacuum. 129.2 g (664 mmol) of 5-chloro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbaldehyde (II-1) in 1 L of DMF were added. The reaction mixture was heated to 150° C. with rapid stirring. The reaction is complete after 3 hours (GC check). The reaction mixture is cooled down to room temperature and bulked with water to a total volume of 4 L. The reaction mixture is washed twice with 2000 ml of ethyl acetate each time. The combined organic phases were subsequently washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated to obtain 117.6 g (90% of theory, purity 90%) of 5-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbaldehyde (IV-1) in the form of a brown solid which is further reacted without further purification.

Workup

  1. temperatureThe reaction mixture is cooled down to room temperature
  2. washThe reaction mixture is washed twice with 2000 ml of ethyl acetate each time
  3. washThe combined organic phases were subsequently washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6a0df86ae8ac4fd18ffde1c93c82acae
Source dataset
uspto-grants-2014_07
Patent number
US08765971B2

Reaction notes

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