Dimethylformamide → 2-(3-Cyano-4-fluorophenyl)acetic acid

HRID 1810093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1810093
Br[C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:13][N:14](C=O)C>C(OCC)(=O)C.O>[C:13]([C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8])#[N:14]

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 34163393-Bromo-4-fluorophenylacetic Acid

Produkt 1

HCID 27739352-(3-Cyano-4-fluorophenyl)acetic acidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

2-(3-Bromo-4-fluorophenyl)acetic acid (64 g, 275 mmol) was diluted with DMF (400 mL) followed by the addition of Cu(I)CN (49 g, 549 mmol). The reaction was heated to 130° C. and stirred for 12 hours. The reaction was allowed to cool and diluted with ethyl acetate and water, and the mixture was filtered. The organic layer was washed with water, 1N HCl, water and the brine. The organic layer was dried over MgSO4, filtered and concentrated to yield 2-(3-cyano-4-fluorophenyl)acetic acid (36 g, 73% yield) as light yellow oil that solidified to a light yellow solid.

Aufarbeitung

  1. temperatureto cool
  2. filtrationthe mixture was filtered
  3. washThe organic layer was washed with water, 1N HCl, water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-659c67d74e7242c898a4cf8622e515cb
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362056B2

Notizen zur Reaktion

Wird geladen…