Pyridine → 2-Fluoro-4-(2-oxoethyl)benzonitrile

HRID 1519628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519628
[CH2:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([F:12])[CH:5]=1)[CH:2]=C.N1C=CC=CC=1.[O:19]=[O+][O-]>C(Cl)Cl.CO>[F:12][C:6]1[CH:5]=[C:4]([CH2:1][CH:2]=[O:19])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 24823OzoneHCID 247217663-(4-Cyano-3-fluorophenyl)-1-propene

Produkt 1

HCID 866944782-Fluoro-4-(2-oxoethyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of 4-allyl-2-fluorobenzonitrile (1 g, 6.2 mmol) in 1:1 CH2Cl2/MeOH (40 mL) containing pyridine (1 mL, 12.4 mmol) was cooled to −78° C., and O3 was passed through until a blue color was present. N2 was then bubbled through to discharge the blue color and Me2S (5 ml) was added. The reaction mixture was allowed to warm and left overnight. The mixture was washed with 1 N HCl and aqueous NaHCO3 and then dried and concentrated to give crude 2-fluoro-4-(2-oxoethyl)benzonitrile. The material was carried on as the crude.

Aufarbeitung

  1. customN2 was then bubbled through
  2. additionwas added
  3. temperatureto warm
  4. washThe mixture was washed with 1 N HCl and aqueous NaHCO3
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-289332fe76a04211aa8fe099e7eb83e7
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073882B2

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