Carbon Dioxide → 2-(4-Cyano-3-(trifluoromethyl)phenyl)acetic acid

HRID 1753086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1753086
C([N-]C(C)C)(C)C.[Li+].[CH3:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=1.[C:22](=[O:24])=[O:23].[Cl-].[NH4+].Cl>C1COCC1.CCOC(C)=O>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([CH2:9][C:22]([OH:24])=[O:23])=[CH:11][C:12]=1[C:18]([F:19])([F:20])[F:21])#[N:15]

Komponenten

8

Edukt 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 27755974-Methyl-2-(trifluoromethyl)benzonitrile

Produkt 1

HCID 708173812-(4-Cyano-3-(trifluoromethyl)phenyl)acetic acidAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Lithium diisopropylamide (13.8 mL, 24.8 mmol, 1.8M in THF) was added to 4-methyl-2-(trifluoromethyl)benzonitrile (2.30 g, 12.4 mmol) in THF (20 mL) at −78° C. and stirred for 5 minutes at −78° C. Excess solid carbon dioxide was added then the mixture was stirred at room temperature for 17 hours. Saturated aqueous ammonium chloride (10.5 mL) and EtOAc (20 mL) was added and the aqueous layer was acidified with 1M HCl. The mixture was extracted with EtOAc (3×15 mL) and the combined organic phases were dried over sodium sulphate and evaporated in vacuo to afford the title compound as a brown oil (88%, 2.52 g).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 17 hours
  2. extractionThe mixture was extracted with EtOAc (3×15 mL)
  3. dry with materialthe combined organic phases were dried over sodium sulphate
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-463c15d2143c44799a32bb1ad0b2fd86
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09163021B2

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