Methanol → 4-chloro-3-(2-fluoro-4-methoxy-5-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole

HRID 1198407Notes

Reaction equation

HRID 1198407 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[C:15](F)=[CH:14][C:13]=2[F:22])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8].[C:23]([O-])([O-])=[O:24].[K+].[K+].CO>O>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[C:15]([O:24][CH3:23])=[CH:14][C:13]=2[F:22])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 152785734-chloro-3-(2,4-difluoro-5-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 152785744-chloro-3-(2-fluoro-4-methoxy-5-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazoleYield 91.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At 35° C., 13.7 g (0.04 mole) 4-chloro-3-(2,4-difluoro-5-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole, 5.5 g (0.04 mole) K2CO3, and 100 mL methanol were stirred for 1 hour. The reaction was cooled, diluted with 100 mL cold water, and extracted four times with ethyl acetate. The ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4, and stripped in vacuo. The residue was purified chromatographically using 25% ethyl acetate in hexane as the eluent to give 13.0 g (90%) of 4-chloro-3-(2-fluoro-4-methoxy-5-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole as a white solid, mp 116° C.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted four times with ethyl acetate
  3. washThe ethyl acetate extracts were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe residue was purified chromatographically

Sources & evidence

ORD record
ord-3a1cd9105d044cc58511572f01b2dcd7
Source dataset
uspto-grants-1994_01
Patent number
US05281571

Reaction notes

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