Isopropenyl acetate → HCID 14368623, Verbindung

HRID 1653835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1653835
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O:18][C:19]([CH3:21])=[CH2:20])(=O)C.C[O-].C([Sn+](CCCC)CCCC)CCC>C1(C)C=CC=CC=1.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH2:20][C:19](=[O:18])[CH3:21])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Komponenten

6

Edukt 3

HCID 7916Isopropenyl acetateHCID 27568764-Bromo-4'-chlorobiphenylHCID 11964040Methoxytri-n-butylstannane

Produkt 1

HCID 14368623HCID 14368623, VerbindungAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178424406HCID 178424406, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-bromo-4'-chlorobiphenyl (16 g; F. R. Shaw and E. E. Turner. J. Chem. Soc., 285 (1932) ), isopropenyl acetate (9 g) and dichlorobis(tri-o-tolylphosphine)palladium (0.47 g) in dry toluene (30 ml), under nitrogen, was added tributyltin methoxide (25.9 ml; Aldrich). The mixture was stirred and heated at 100° for 5 hr, cooled and the solvent evaporated in vacuo. The residue was chromatographed on silica gel, eluting with cyclohexane then ether. The resultant solid was recrystallised from cyclohexane to afford the title compound (10 g), m.p. 79°-81°.

Aufarbeitung

  1. temperatureheated at 100° for 5 hr
  2. temperaturecooled
  3. customthe solvent evaporated in vacuo
  4. customThe residue was chromatographed on silica gel
  5. washeluting with cyclohexane
  6. customThe resultant solid was recrystallised from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-e9b9488455b64804a38a0559ad86553b
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05403934

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