1,3-Diphenylisobenzofuran → 3-Bromo-7,12-diphenylbenzo[k]fluoranthene

HRID 919180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 919180
[C:1]1([C:7]2O[C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]3[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:22][C:23]1[C:33]2[C:34]3[C:26]([CH:27]=[CH:28][C:29]=3[CH:30]=[CH:31][CH:32]=2)=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[Br:22][C:23]1[CH:24]=[CH:25][C:26]2=[C:34]3[C:33]=1[CH:32]=[CH:31][CH:30]=[C:29]3[C:28]1[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]3=[C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:27]=12

Komponenten

4

Edukt 2

HCID 216491,3-DiphenylisobenzofuranHCID 122444035-Bromoacenaphthylene

Produkt 1

HCID 107909823-Bromo-7,12-diphenylbenzo[k]fluorantheneAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 14.9 g (55.2 mmol) of 1,3-diphenylisobenzofuran, 12.8 g (55.2 mmol) of 5-bromoacenaphthylene, and 50 mL of toluene was stirred for 16 hours under heat refluxing. After distilling off the solvent, 1,200 mL of acetic acid was added, and the mixture was heated at 80° C. To this mixture, 150 mL of a 48% HBr aqueous solution was added, and the mixture was stirred at 80° C. for one hour. After cooling the resultant mixture to room temperature, a precipitate was collected by filtration and washed with methanol. The resulting yellow solid was recrystallized from 200 mL of toluene. A crystal was collected by filtration to obtain 19.8 g (yield: 74%) of 3-bromo-7,12-diphenylbenzo[k]fluoranthene as a yellow solid.

Aufarbeitung

  1. temperatureunder heat
  2. temperaturerefluxing
  3. distillationAfter distilling off the solvent, 1,200 mL of acetic acid
  4. additionwas added
  5. additionTo this mixture, 150 mL of a 48% HBr aqueous solution was added
  6. stirringthe mixture was stirred at 80° C. for one hour
  7. temperatureAfter cooling the resultant mixture to room temperature
  8. filtrationa precipitate was collected by filtration
  9. washwashed with methanol
  10. customThe resulting yellow solid was recrystallized from 200 mL of toluene
  11. filtrationA crystal was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-739d09d02b624b4cbf1f7330d265667b
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273002B2

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