Thionyl Chloride → 5-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbonyl chloride

HRID 2206851Notes

Reaction equation

HRID 2206851 reaction equation
[F:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([F:10])[F:9])[C:3]=1[C:11]([OH:13])=O.S(Cl)([Cl:16])=O>>[F:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([F:10])[F:9])[C:3]=1[C:11]([Cl:16])=[O:13]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 231925843-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 529205085-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbonyl chloride

Procedure

9.1 g of 5-fluoro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid and 75.5 mL of thionyl chloride were heated under reflux for 1.5 h. After cooling, the reaction mixture was concentrated under reduced pressure, giving 10 g of 5-fluoro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride as a yellow oil.

Workup

  1. temperatureunder reflux for 1.5 h
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bee36f8caf8f46d2bddd1dfc96760580
Source dataset
uspto-grants-2016_06
Patent number
US09375004B2

Reaction notes

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