Reaktion #48715

ord-a207859cfb484bf3b0098ee913e5b2b4

Reaktionsgleichung

O
water
CC(=O)[O-].[NH4+]
ammonium acetate
CCCOc1cc(F)cc(C=O)c1
3-fluoro-5-propoxy-benzaldehyde
C[N+](=O)[O-]
nitromethane
→
CCCOc1cc(F)cc(/C=C/[N+](=O)[O-])c1
desired compound
Ausbeute 69.8%
CCCOc1cc(F)cc(/C=C/[N+](=O)[O-])c1
1-Fluoro-3-((E)-2-nitro-vinyl)-5-propoxy-benzene
Ausbeute 69.8%

Edukte

O
water
CC(=O)[O-].[NH4+]
ammonium acetate
CCCOc1cc(F)cc(C=O)c1
3-fluoro-5-propoxy-benzaldehyde
C[N+](=O)[O-]
nitromethane

Reagenzien

Keine

Lösungsmittel

CC(=O)O
acetic acid

Reaktionsbedingungen

Temperatur
140°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturCool to room temperature
  2. 2
    ExtraktionExtract with ethyl acetate
  3. 3
    Trocknendry over magnesium sulfate
  4. 4
    Filtrationfilter
  5. 5
    Einengenconcentrate

Vorschrift

Add ammonium acetate (2.63 g, 34.08 mmol) to 3-fluoro-5-propoxy-benzaldehyde (2.25 g, 12.35 mmol) and nitromethane (3.09 g, 50.63 mmol) in acetic acid (41 mL) at room temperature and heat in 140° C. oil bath for 3 hours. Cool to room temperature and pour into water. Extract with ethyl acetate, dry over magnesium sulfate, filter and concentrate to afford 1.94 g (69.8%) of the desired compound as an oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745438B2uspto-grants-2010_06