Hydrochloric Acid → 4,4,4-Trifluoro-1-(4-fluorophenyl)butane-1,3-dione

HRID 1994278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1994278
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=1.Cl>C(OC)(C)(C)C>[F:9][C:2]([F:1])([F:8])[C:3](=[O:5])[CH2:21][C:20]([C:17]1[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=1)=[O:22]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 98284'-FluoroacetophenoneHCID 10942334Sodium Methoxide

Produkt 1

HCID 27714764,4,4-Trifluoro-1-(4-fluorophenyl)butane-1,3-dioneAusbeute 823,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15413tert-Butyl methyl etherLösungsmittel2×

Versuchsvorschrift

Ethyl trifluoroacetate (2.35 g, 1.66 mmol) was placed in a 50 mL round bottom flask, and dissolved in methyl tert-butyl ether (7.5 mL). To the stirred solution was added 25 weight % sodium methoxide (4.0 mL, 17.7 mmol) via an addition funnel over a 2 minute period. Next, 4′-fluoroacetophenone (2.1 g, 15 mmol) was dissolved in methyl tert-butyl ether (2 mL), and added to the reaction dropwise over 5 minutes. After stirring overnight (15.75 hours), 3N HCl (7.0 mL) was added. The organic layer was collected, washed with brine (7.5 mL), dried over MgSO4, filtered, and concentrated in vacuo to give 3.2 g of pale-orange solid. The solid was recrystallized from iso-octane to give 2.05 g of the dione.

Aufarbeitung

  1. additionadded to the reaction dropwise over 5 minutes
  2. additionwas added
  3. customThe organic layer was collected
  4. washwashed with brine (7.5 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-763cbc3217884b9abb0561357ed92a22
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652149B2

Notizen zur Reaktion

Wird geladen…