تفاعل #81605

معادلة التفاعل

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

acrylamide

tri-o-tolylphosphine

triethylamine

→

title compound

المردود 59.4%

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

المردود 59.4%

المذيبات

acetonitrile

dichloromethane

Water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled
2. 2
   درجة الحرارةthe mixture was warmed
3. 3
   workup.ADDITIONto disperse the solid residue
4. 4
   درجة الحرارةThe mixture was cooled
5. 5
   ترشيحfiltered
6. 6
   workup.DISSOLUTIONthe solid was dissolved in hot isopropanol (500 ml)
7. 7
   ترشيحThe solution was filtered hot
8. 8
   تركيزthe filtrate was concentrated until crystallisation
9. 9
   workup.ADDITIONAn equal volume of ether was added
10. 10
    درجة الحرارةto cool
11. 11
    ترشيحThe solid was filtered off
12. 12
    أخرىdried

الإجراء التجريبي

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%.

المصدر