Methanol → 4-(4-Fluoro-phenyl)-3-(4-methanesulfonyl-phenyl)-5-trifluoromethyl-1H-pyrazole

HRID 375653Notes

Reaction equation

HRID 375653 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][C:20](SC)=[CH:19][CH:18]=3)=[N:10][NH:11][C:12]=2[C:13]([F:16])([F:15])[F:14])=[CH:4][CH:3]=1.O[O:26][S:27]([O-:29])=O.[K+].[CH3:31]O>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:17]3[CH:18]=[CH:19][C:20]([S:27]([CH3:31])(=[O:29])=[O:26])=[CH:21][CH:22]=3)=[N:10][NH:11][C:12]=2[C:13]([F:14])([F:16])[F:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 153802214-(4-fluorophenyl)-3-[4-(methylthio)phenyl]-5-(trifluoromethyl)-1H-pyrazoleHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 153802224-(4-Fluoro-phenyl)-3-(4-methanesulfonyl-phenyl)-5-trifluoromethyl-1H-pyrazoleYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of the pyrazole from Step 2 (4.0 g, 11.4 mmol) in 150 mL methanol was added a solution of Oxone® (14.0 g, 22.7 mmol) in 50 mL water. After 1 hour the solids were filtered off, washed with ethyl acetate and the filtrate concentrated in vacuo. This mixture was partitioned between ethyl acetate and water, and the organic layer washed with brine, dried over MgSO4 and reconcentrated in vacuo. Recrystallization from chloroform gave 4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazole (3.98 g, 91%) as a pale yellow solid: mp 219°-220° C. Elemental analysis for C17H12N2F4SO2Calc'd.: C, 53.12, H, 3.15, N, 7.29, S, 8.34. Found: C, 52.85, H, 3.12, N, 7.21, S, 8.61

Workup

  1. filtrationAfter 1 hour the solids were filtered off
  2. washwashed with ethyl acetate
  3. concentrationthe filtrate concentrated in vacuo
  4. customThis mixture was partitioned between ethyl acetate and water
  5. washthe organic layer washed with brine
  6. dry with materialdried over MgSO4
  7. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-8aa20b5e63724886b8c425bcc35f595d
Source dataset
uspto-grants-1996_01
Patent number
US05486534

Reaction notes

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