Ethanol → 3-Ethenyl-2,6-difluorobenzonitrile

HRID 1502010Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1502010
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([C:14]#[N:15])[C:8]=1[F:16])(=O)=O.[CH2:19](O)[CH3:20]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH:19]([C:7]1[C:8]([F:16])=[C:9]([C:10]([F:13])=[CH:11][CH:12]=1)[C:14]#[N:15])=[CH2:20]

Komponenten

4

Edukt 2

HCID 702EthanolHCID 867270593-Cyano-2,4-difluorophenyl trifluoromethanesulfonate

Produkt 1

HCID 867270603-Ethenyl-2,6-difluorobenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418807HCID 178418807, VerbindungKatalysator

Versuchsvorschrift

3-Cyano-2,4-difluorophenyl trifluoromethanesulfonate (5.20 g, 18.1 mmol), potassium vinyl trifluoroborate (4.85 g, 36.2 mmol), PdCl2(dppf)-CH2Cl2 Adduct (0.662 g, 0.905 mmol), and TEA (5.05 mL, 36.2 mmol) were added to 75 mL of ethanol. The reaction mixture was degassed then heated at reflux for 4 h. LC-MS analysis confirmed product peak. The reaction mixture was diluted with ethyl acetate, washed twice with brine, dried, and evaporated to dryness. The crude material was then purified by MPLC chromatography through a 330 g Redi-sep column eluting with 10% EtOAc/Hexane solvent system to yield 3-ethenyl-2,6-difluorobenzonitrile.

Aufarbeitung

  1. customThe reaction mixture was degassed
  2. temperaturethen heated
  3. temperatureat reflux for 4 h
  4. additionThe reaction mixture was diluted with ethyl acetate
  5. washwashed twice with brine
  6. customdried
  7. customevaporated to dryness
  8. customThe crude material was then purified by MPLC chromatography through a 330 g Redi-sep column
  9. washeluting with 10% EtOAc/Hexane solvent system

Quellen und Nachweise

ORD-Eintrag
ord-ea8dbff2fa5d4f8b89cf845585d25a44
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206199B2

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