N-bromobutanimide → Ethyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-bromomethylpyrazole-3-carboxylate

HRID 377638Notes

Reaction equation

HRID 377638 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])[N:19]=[C:18]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:17]=2[CH3:34])=[CH:12][CH:11]=1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])[N:19]=[C:18]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:17]=2[CH2:34][Br:1])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 10938462Ethyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 19356248Ethyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-bromomethylpyrazole-3-carboxylateYield 110.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

4.8 g of N-bromosuccinimide and 20 mg of benzoyl peroxide are added to a solution of 10.73 g of ethyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylate in 200 ml of CCl4 and the mixture is then refluxed for 16 hours. The insoluble material is filtered off and the filtrate is concentrated under vacuum. The residue is extracted with DCM, the organic phase is washed with water and dried over MgSO4 and the solvent is evaporated off under vacuum to give 14.13 g of the expected product.

Workup

  1. temperaturethe mixture is then refluxed for 16 hours
  2. filtrationThe insoluble material is filtered off
  3. concentrationthe filtrate is concentrated under vacuum
  4. extractionThe residue is extracted with DCM
  5. washthe organic phase is washed with water
  6. dry with materialdried over MgSO4
  7. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-97ab40c8b566468d93deee4bf08d21a8
Source dataset
uspto-grants-2000_02
Patent number
US06028084

Reaction notes

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