Diethyl Ether → 4-bromo-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylic acid

HRID 1256584Notes

Reaction equation

HRID 1256584 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]([OH:23])=[O:22])[CH:9]=2)=[CH:4][CH:3]=1.[Br:24]Br.C(OCC)C.C([O-])(O)=O.[Na+]>ClCCl>[Br:24][C:9]1[C:10]([C:21]([OH:23])=[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

6

Reactant 4

HCID 3283Diethyl EtherHCID 24408BromineHCID 516892Sodium BicarbonateHCID 14772405-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 668445074-bromo-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylic acidYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylic acid (20.0 g, 54.5 mmol) in dichloromethane (400 ml) was slowly added bromine (5.62 ml, 109 mmol) and the resulting mixture was reacted for 16 hours at room temperature. Diethyl ether (400 ml) and excess aqueous saturated NaHCO3 solution were successively added. The organic layer was separated, twice washed with aqueous saturated NaHCO3 solution and subsequently washed with brine, dried over MgSO4, filtered and concentrated to give 4-bromo-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylic acid (19.77 gram, 81% yield). Melting point: 222-224° C.

Workup

  1. customthe resulting mixture was reacted for 16 hours at room temperature
  2. customThe organic layer was separated
  3. washtwice washed with aqueous saturated NaHCO3 solution
  4. washsubsequently washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-08aa7a21977f47fc91b8e8bcf0182414
Source dataset
uspto-grants-2013_06
Patent number
US08461184B2

Reaction notes

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