Potassium Carbonate → 2-Fluoro-4-(3,3,3-trifluoropropoxy)benzoic acid

HRID 1799289Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1799289
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:9]=1[C:10]([O:12]C)=[O:11].FC(F)(F)S(O[CH2:25][CH2:26][C:27]([F:30])([F:29])[F:28])(=O)=O>CC(=O)CC>[F:7][C:8]1[CH:17]=[C:16]([O:18][CH2:25][CH2:26][C:27]([F:30])([F:29])[F:28])[CH:15]=[CH:14][C:9]=1[C:10]([OH:12])=[O:11]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 141328493,3,3-Trifluoropropyl trifluoromethanesulfonateHCID 22463192Methyl 2-fluoro-4-hydroxybenzoate

Produkt 1

HCID 690190042-Fluoro-4-(3,3,3-trifluoropropoxy)benzoic acidAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Potassium carbonate (663 mg) was added to a 2-butanone (6 mL) solution of methyl 2-fluoro-4-hydroxybenzoate (compound described in U.S. Pat. No. 5,990,142 A1, 340 mg) and 3,3,3-trifluoropropyl trifluoromethanesulfonate (compound described in Tetrahedron, (1988), 44, 5375-5388, 590 mg). The mixture was stirred at 75° C. for 1.5 hours, and then the solvent was evaporated. To the obtained residue were added methanol (8 mL) and a 2 M sodium hydroxide aqueous solution (2 mL). The mixture was stirred at 60° C. for 1.5 hours, and the solvents (mainly methanol) were evaporated. To the residue was added water (15 mL), and the mixture was changed to acidic by adding 1 M hydrochloric acid thereto while stirring. The precipitated crystalline solid was collected by filtration, washed with water, and dried under reduced pressure to give 203 mg of the title compound (white crystal, yield: 40%).

Aufarbeitung

  1. customthe solvent was evaporated
  2. additionTo the obtained residue were added methanol (8 mL)
  3. stirringThe mixture was stirred at 60° C. for 1.5 hours
  4. customthe solvents (mainly methanol) were evaporated
  5. additionTo the residue was added water (15 mL)
  6. additionby adding 1 M hydrochloric acid
  7. stirringwhile stirring
  8. filtrationThe precipitated crystalline solid was collected by filtration
  9. washwashed with water
  10. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2a54e945e3714da5b677085c8ed7f732
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344029B2

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