Carbon Tetrachloride → 1-(3-Cyano-4-fluorophenyl)-3-trifluoromethyl-5-hydroxycarbonylpyrazole

HRID 1768105Notes

Reaction equation

HRID 1768105 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[O:14]C=CC=3)=[CH:11][C:10]([C:18]([F:21])([F:20])[F:19])=[N:9]2)=[CH:4][C:3]=1[C:22]#[N:23].C(Cl)(Cl)(Cl)Cl.I([O-])(=O)(=O)=[O:30].[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:30])=[O:14])=[CH:11][C:10]([C:18]([F:21])([F:20])[F:19])=[N:9]2)=[CH:4][C:3]=1[C:22]#[N:23]

Participants

7

Reactant 3

HCID 5943Carbon TetrachlorideHCID 104487241-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-(2-furyl)pyrazoleHCID 23667635Sodium periodate

Product 1

HCID 104700071-(3-Cyano-4-fluorophenyl)-3-trifluoromethyl-5-hydroxycarbonylpyrazoleYield 64.2%

Reagents, catalysts & solvents 3

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(4-fluoro-3-cyanophenyl)-3-trifluoromethyl-5-(2-furyl)pyrazole (4.0 g, 12.5 mmol) in acetonitrile (30 mL) was added carbon tetrachloride (30 mL), ruthenium chloride (0.4 g) and a solution of sodium periodate (11.9 g, 56.1 mmol) in water (45 mL). The reaction is stirred at room temperature overnight. The next day the reaction mixture was filtered through celite. The filtrate was concentrated and partitioned between ethyl acetate and HCl (1N). The organic phase was washed with water, dried over sodium sulfate, filtered and concentrated to give 1-(4-fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxycarbonyl pyrazole (2.4 g, 64% yield) as pure compound. MS (ES−): 298 (M−H)− (40%).

Workup

  1. filtrationThe next day the reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. custompartitioned between ethyl acetate and HCl (1N)
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0221c82403da43f99afa4560b0d80866
Source dataset
uspto-grants-2007_06
Patent number
US07235575B2

Reaction notes

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