Benzoyl Peroxide → Methyl 4-(bromomethyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylate

HRID 1593540Notes

Reaction equation

HRID 1593540 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([O:23][CH3:24])=[O:22])[C:9]=2[CH3:25])=[CH:4][CH:3]=1.C1C(=O)N([Br:33])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:33][CH2:25][C:9]1[C:10]([C:21]([O:23][CH3:24])=[O:22])=[N:11][N:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 19356244Methyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylate

Product 1

HCID 10994377Methyl 4-(bromomethyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylateYield 85.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

19 g of methyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate is placed in 200 ml of CCl4 and 8.54 g of NBS and then 1 g of benzoyl peroxide are added, heating under reflux overnight. On returning to RT, the precipitate that forms is filtered and washed with CCl4. All of the filtrate is evaporated, then taken up in AcOEt and washed with saturated NaCl solution (twice). It is dried over MgSO4 and evaporated. The expected compound crystallizes in iso ether, it is filtered and dried to obtain 19.4 g of the expected compound.

Workup

  1. temperatureheating
  2. temperatureunder reflux overnight
  3. customOn returning to RT
  4. filtrationthe precipitate that forms is filtered
  5. washwashed with CCl4
  6. customAll of the filtrate is evaporated
  7. washwashed with saturated NaCl solution (twice)
  8. dry with materialIt is dried over MgSO4
  9. customevaporated
  10. customThe expected compound crystallizes in iso ether, it
  11. filtrationis filtered
  12. customdried

Sources & evidence

ORD record
ord-9bdd950d889a46e6a9588e470f744a63
Source dataset
uspto-grants-2007_11
Patent number
US07297710B1

Reaction notes

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