Chloroform → 2-(2-Chloro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride

HRID 1672997Notes

Reaction equation

HRID 1672997 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13](O)=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[N:9]1.C(Cl)(Cl)[Cl:21].C(Cl)(=O)C(Cl)=O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]([Cl:21])=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[N:9]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 65578Oxalyl chlorideHCID 179605961-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 574582382-(2-Chloro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a N2 purged round bottom flask was added 2-(2-chlorophenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid (2.10 g, 7.20 mmol) and anhydrous CHCl3 (30 mL). The solution was cooled to 0° C. prior to the addition of oxalyl chloride (1.3 mL, 14 mmol) and anhydrous DMF (1 mL). The reaction solution was stirred 1 h under N2. The solution was concentrated under reduced pressure on the rotavapor to afford 2.4 g crude product. The crude acid chloride was used without further purification in the next reaction step.

Workup

  1. concentrationThe solution was concentrated under reduced pressure on the rotavapor

Sources & evidence

ORD record
ord-e91d82c26b3a449a8a33e56c7a3b97e1
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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