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2-(4-Bromophenyl)ethanol → 2-{2-[4-(2-Hydroxy-ethyl)phenyl]-vinyl}-isoindole-1,3-dione

HRID 2383368
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2383368
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH:20]([N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32])=[CH2:21].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C>[OH:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH:21]=[CH:20][N:22]2[C:23](=[O:32])[C:24]3[C:25](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]2=[O:27])=[CH:3][CH:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 728512-(4-Bromophenyl)ethanolHCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 80271Tri-o-tolylphosphineHCID 81531Diisopropylethylamine

Produkt 1

HCID 670291452-{2-[4-(2-Hydroxy-ethyl)phenyl]-vinyl}-isoindole-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 2-(4-bromophenyl)ethanol (48.3 g) in acetonitrile (480 mL) was added diisopropylethylamine (46.6 g), N-vinylphthalimide (43.7 g) and tri-o-tolylphosphine (7.31 g) and the mixture was purged with nitrogen gas three times. Palladium acetate (2.7 g) was added and the mixture was stirred at 90° C. for 21 hr under nitrogen. The reaction was cooled and the precipitated product collected by filtration. The resulting solid was re-dissolved in dichloromethane and ethyl acetate and filtered through silica gel. The filtrate was concentrated in vacuo to give the title compound, 24 g.

Aufarbeitung

  1. customthe mixture was purged with nitrogen gas three times
  2. additionPalladium acetate (2.7 g) was added
  3. temperatureThe reaction was cooled
  4. filtrationthe precipitated product collected by filtration
  5. dissolutionThe resulting solid was re-dissolved in dichloromethane
  6. filtrationethyl acetate and filtered through silica gel
  7. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-18504441bd204a2089c41bc9ea38e454
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08263623B2

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