반응 #81605

반응 방정식

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

acrylamide

tri-o-tolylphosphine

triethylamine

→

title compound

수율 59.4%

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

수율 59.4%

용매

acetonitrile

dichloromethane

Water

반응 조건

후처리

1. 1
   온도cooled
2. 2
   온도the mixture was warmed
3. 3
   workup.ADDITIONto disperse the solid residue
4. 4
   온도The mixture was cooled
5. 5
   여과filtered
6. 6
   workup.DISSOLUTIONthe solid was dissolved in hot isopropanol (500 ml)
7. 7
   여과The solution was filtered hot
8. 8
   농축the filtrate was concentrated until crystallisation
9. 9
   workup.ADDITIONAn equal volume of ether was added
10. 10
    온도to cool
11. 11
    여과The solid was filtered off
12. 12
    기타dried

실험 절차

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%.

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