3-Bromo-4-fluorophenylacetic Acid → 2-(3-Cyano-4-fluorophenyl)acetic acid

HRID 82189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 82189
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].[Cu][C:14]#[N:15]>CN(C=O)C.C(OCC)(=O)C>[C:14]([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:15]

Komponenten

5

Edukt 2

HCID 34163393-Bromo-4-fluorophenylacetic AcidHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 27739352-(3-Cyano-4-fluorophenyl)acetic acidAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a solution of (3-bromo-4-fluoro-phenyl)-acetic acid (10 g, 42.9 mmol) in DMF (65 mL) was added copper (I) cyanide (7.7 g, 85.8 mmol) and heated at 130° C. for 24 hrs. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (250 mL). The organic layer was washed with water (5×50 mL), brine (50 mL), dried over sodium filtered and concentrated under reduced pressure. The crude material was re-crystallized from diethyl ether and hexane to afford the title compound as a yellow solid in 65% yield, 5 g.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed with water (5×50 mL), brine (50 mL)
  3. dry with materialdried over sodium
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was re-crystallized from diethyl ether and hexane

Quellen und Nachweise

ORD-Eintrag
ord-71110d3367f44455ae029b040795aa29
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846698B2

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