Reaktion #81605

Reaktionsgleichung

ethyl 3-[3-bromo-5-[(4-fluorophenyl)hydroxymethyl]phenyl]-2-propenoate

acrylamide

tri-o-tolylphosphine

triethylamine

→

title compound

Ausbeute 59.4%

Ethyl 3-[3-(2-carbamoylethenyl)-5-[(4-fluorophenyl)-hydroxymethyl]phenyl]2-propenoate

Ausbeute 59.4%

Lösungsmittel

acetonitrile

dichloromethane

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   Temperaturthe mixture was warmed
3. 3
   workup.ADDITIONto disperse the solid residue
4. 4
   TemperaturThe mixture was cooled
5. 5
   Filtrationfiltered
6. 6
   workup.DISSOLUTIONthe solid was dissolved in hot isopropanol (500 ml)
7. 7
   FiltrationThe solution was filtered hot
8. 8
   Einengenthe filtrate was concentrated until crystallisation
9. 9
   workup.ADDITIONAn equal volume of ether was added
10. 10
    Temperaturto cool
11. 11
    FiltrationThe solid was filtered off
12. 12
    Sonstigedried

Vorschrift

A mixture of ethyl 3-[3-bromo-5-[(4-fluorophenyl)hydroxymethyl]phenyl]-2-propenoate (9.50 g), acrylamide (2.67 g), palladium(II) acetate (0.306 g), tri-o-tolylphosphine (0.763 g) and triethylamine (3.80 g) in acetonitrile (10 ml) was heated to 100° C. for 4 hours under an atmosphere of nitrogen and then cooled. Water (150 ml) and dichloromethane (150 ml) was added and the mixture was warmed with stirring to disperse the solid residue. The mixture was cooled and filtered, and the solid was dissolved in hot isopropanol (500 ml). The solution was filtered hot using a filter aid, and the filtrate was concentrated until crystallisation commenced. An equal volume of ether was added and the mixture was allowed to cool. The solid was filtered off and dried to give the title compound (5.50 g), m.p. 197°-199° C. Found: C,68.55; H,5.17; N,4.01. C21H20FNO4 requires C,68.28; H,5.46; N,3.79%.

Quelle