Benzoyl Peroxide → 1-(3-bromomethyl-4-chlorophenyl)-3-(3-chlorophenyl)-1H-pyrazole

HRID 70255Notes

Reaction equation

HRID 70255 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Br:21]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 667871901-(3-methyl-4-chlorophenyl)-3-(3-chlorophenyl)-1H-pyrazole2×

Product 1

HCID 667879841-(3-bromomethyl-4-chlorophenyl)-3-(3-chlorophenyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1-(3-methyl-4-chlorophenyl)-3-(3-chlorophenyl)-1H-pyrazole (i.e. the product of Step A) (1.7 g, 5.61 mmol), N-bromosuccinimide (1.1 g, 6.17 mmol) and benzoyl peroxide (30 mg, 0.12 mmol) in 100 mL of carbon tetrachloride was irradiated with a sun lamp for 4 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by medium pressure liquid chromatography (10 to 20% gradient of ethyl acetate in hexanes as eluant) to give the title compound as a white solid (0.37 g).

Workup

  1. customwas irradiated with a sun lamp for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by medium pressure liquid chromatography (10 to 20% gradient of ethyl acetate in hexanes as eluant)

Sources & evidence

ORD record
ord-ca3f81fd00284213a9c3f5440e5bac16
Source dataset
uspto-grants-2014_09
Patent number
US08822521B2

Reaction notes

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