1-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethylpyrazole → 1-(3-Cyano-4-fluorophenyl)-3-trifluoromethyl-5-hydroxycarbonylpyrazole

HRID 1768104Notes

Reaction equation

HRID 1768104 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][OH:14])=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[N:9]2)=[CH:4][C:3]=1[C:19]#[N:20].I([O-])(=O)(=O)=[O:22].[Na+]>C(#N)C.O.[Ru](Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([OH:22])=[O:14])=[CH:11][C:10]([C:15]([F:17])([F:16])[F:18])=[N:9]2)=[CH:4][C:3]=1[C:19]#[N:20]

Participants

6

Reactant 2

HCID 222807401-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethylpyrazoleHCID 23667635Sodium periodate

Product 1

HCID 104700071-(3-Cyano-4-fluorophenyl)-3-trifluoromethyl-5-hydroxycarbonylpyrazoleYield 57.1%

Reagents, catalysts & solvents 3

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(4-fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethylpyrazole (0.45 g, 1.58 mmol) in acetonitrile (10 mL) was added catalytic amount of ruthenium chloride at 0° C. followed by addition of a solution sodium periodate (0.71 g, 3.32 mmol) in water. The reaction was stirred at 0° C. to room temperature overnight. The next day the acetonitrile was evaporated and the residue was partitioned between ethyl acetate and water, washed with brine, dried over sodium sulfate, filtered and concentrated to give 1-(4-fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxycarbonylpyrazole (0.27 g, 57% yield) as pure compound: MS (ES−): 298 (M−H)− (40%).

Workup

  1. customThe next day the acetonitrile was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5e3a2e6a12e8452498230ebbe27f7c6b
Source dataset
uspto-grants-2007_06
Patent number
US07235575B2

Reaction notes

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