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

HRID 631033Notes

Reaction equation

HRID 631033 reaction equation
[F:1][CH:2]([F:13])[C:3]1[C:7]([C:8](O)=[O:9])=[C:6]([F:11])[N:5]([CH3:12])[N:4]=1.S(Cl)([Cl:16])=O>>[F:1][CH:2]([F:13])[C:3]1[C:7]([C:8]([Cl:16])=[O:9])=[C:6]([F:11])[N:5]([CH3:12])[N:4]=1

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 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxylic acid and 75.5 mL of thionyl chloride are refluxed for 1.5 hours. After cooling down, the reaction mixture is evaporated under vacuum to yield 10 g of 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl chloride as a yellow oil. GC-MS; observed M/z: Molecular ion: (M+.)=212; fragments: (M+.−Cl)=177 and (M+.−F)=193.

Workup

  1. temperatureAfter cooling down
  2. customthe reaction mixture is evaporated under vacuum

Sources & evidence

ORD record
ord-7de0443b8fce4302972c473d73880833
Source dataset
uspto-grants-2016_04
Patent number
US09320276B2

Reaction notes

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