Thionyl Chloride → 3-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chloride

HRID 2089555Notes

Reaction equation

S(Cl)([Cl:3])=O.[F:5][CH:6]([F:16])[C:7]1[C:11]([C:12](O)=[O:13])=[CH:10][N:9]([CH3:15])[N:8]=1>ClC1C=CC=CC=1>[F:5][CH:6]([F:16])[C:7]1[C:11]([C:12]([Cl:3])=[O:13])=[CH:10][N:9]([CH3:15])[N:8]=1

Participants

Conditions

Temperature: 110 °C

Procedure

69.5 g of thionyl chloride (0.58 mol, 1.17 equivalents) are added at 110° C. in the course of 2 hours to a solution of 88 g of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (0.5 mol) in 440 g of chlorobenzene. The reaction mixture is stirred for 1 hour at 110° C. The reaction mixture is concentrated to a crude product solution. 190 g of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (50% in chlorobenzene, yield: 98%) is obtained. The crude product solution is used without being further purified.

Workup

concentrationThe reaction mixture is concentrated to a crude product solution

Sources & evidence

ORD record: ord-d3a557808d8e48f1af7894d0426e20e3
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436037B2

Reaction notes

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