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

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

Reactant 2

HCID 24386Thionyl Chloride

HCID 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 refluxed for 1.5 hours. After cooling down, the reaction mixture was evaporated under vacuum to yield 10 g of 5-fluoro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride as a yellow oil.

Workup

temperatureAfter cooling down
customthe reaction mixture was evaporated under vacuum

Sources & evidence

ORD record: ord-699262d78a1b469f8eec4cfe9a3016f3
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653114B2

Reaction notes

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