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

HRID 1768105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1768105
[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]

Komponenten

7

Edukt 3

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

Produkt 1

HCID 104700071-(3-Cyano-4-fluorophenyl)-3-trifluoromethyl-5-hydroxycarbonylpyrazoleAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 61850Ruthenium trichlorideKatalysatorHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0221c82403da43f99afa4560b0d80866
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235575B2

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