Réaction #48637

Équation de réaction

3-chloro-5-fluorobenzaldehyde

nitromethane

ammonium acetate

→

desired compound

Rendement 58.5%

1-Chloro-3-fluoro-5-((E)-2-nitrovinyl)-benzene

Rendement 58.5%

Solvants

acetic acid

sodium hydroxide

Conditions de réaction

Traitement

1. 1
   Températureto reflux for 4 hours
2. 2
   TempératureCool
3. 3
   workup.ADDITIONpour over ice
4. 4
   Extractionextract with ethyl acetate
5. 5
   Séchagedry (magnesium sulfate)
6. 6
   Concentrationconcentrate
7. 7
   Autrepurify
8. 8
   Lavage(silica gel chromatography, eluting with 1:1 dichloromethane:hexanes)

Mode opératoire

Dissolve 3-chloro-5-fluorobenzaldehyde (4.0 g, 25.2 mmol) in glacial acetic acid (15 mL). Add nitromethane (4.1 mL, 75.7 mmol) and ammonium acetate (1.94 g, 25.2 mmol) and heat to reflux for 4 hours. Cool and pour over ice. Dilute with 2 N sodium hydroxide and extract with ethyl acetate, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 1:1 dichloromethane:hexanes) to give the desired compound as a beige solid (2.97 g, 58%).

Source