Trifluoroacetic acid → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-fluoromethyl-4-trifluoromethylsulfinylpyrazole

HRID 523460Notes

Reaction equation

HRID 523460 reaction equation
FC(F)(F)C(O)=[O:4].[C:8]([C:10]1[C:14]([S:15][C:16]([F:19])([F:18])[F:17])=[C:13]([CH2:20][F:21])[N:12]([C:22]2[C:27]([Cl:28])=[CH:26][C:25]([C:29]([F:32])([F:31])[F:30])=[CH:24][C:23]=2[Cl:33])[N:11]=1)#[N:9]>OO>[C:8]([C:10]1[C:14]([S:15]([C:16]([F:18])([F:17])[F:19])=[O:4])=[C:13]([CH2:20][F:21])[N:12]([C:22]2[C:27]([Cl:28])=[CH:26][C:25]([C:29]([F:32])([F:31])[F:30])=[CH:24][C:23]=2[Cl:33])[N:11]=1)#[N:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 247854673-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-fluoromethyl-4-trifluoromethylthiopyrazole

Product 1

HCID 247857393-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-fluoromethyl-4-trifluoromethylsulfinylpyrazoleYield 32%

Reagents, catalysts & solvents 1

HCID 784Hydrogen PeroxideSolvent

Procedure

A 30 wt % aqueous solution of hydrogen peroxide (50 μL) was added to a trifluoroacetic acid solution of 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-fluoromethyl-4-trifluoromethylthiopyrazole (205 mg) prepared as described in Example 30. The reaction mixture was stirred for 6 h whereupon solvent was evaporated under reduced pressure to give a residue that was purified by chromatography (SiO2, heptane/DCM) to afford the title compound as a white solid (66.5 mg, 32%). MS (ES): M/Z [M−H] 452. 1H NMR: (400 MHz, DMSO-d6): 5.48-5.75 (m, 2H) and 8.41 (s, 2H). 19F NMR (376 MHz, DMSO-d6): −62.05 (s, 3F), −73.68 (d, 3F) and −82.41 (m, 1F).

Workup

  1. customprepared
  2. customwas evaporated under reduced pressure
  3. customto give a residue that
  4. customwas purified by chromatography (SiO2, heptane/DCM)

Sources & evidence

ORD record
ord-6d9d1b4016504f67a1fbc8f8828511f6
Source dataset
uspto-grants-2016_05
Patent number
US09339033B2

Reaction notes

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