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

HRID 1012678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012678
[Br:1][C:2]1[C:12]2[C:13]3[C:5]([CH:6]=[CH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.[C:14]1([C:20]2O[C:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:23]3[C:28]=2[CH:27]=[CH:26][CH:25]=[CH:24]3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[C:12]2[C:13]3[C:5]([C:6]4[C:20]([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)=[C:28]5[CH:27]=[CH:26][CH:25]=[CH:24][C:23]5=[C:22]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:7]=4[C:8]=3[CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 216491,3-DiphenylisobenzofuranHCID 122444035-Bromoacenaphthylene

Produkt 1

HCID 107909823-Bromo-7,12-diphenylbenzo[k]fluorantheneAusbeute 52,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel2×

Versuchsvorschrift

200 ml of xylene was added to a mixture of 5-bromoacenaphthylene (14.5 g, 62.8 mmol) and diphenylisobenzofuran (17.1 g, 63.3 mmol), and stirred for 5 hours under reflux of xylene. The mixture obtained was cooled to room temperature, and thereafter the solvent was distilled off, and 26 ml of trifluoroacetic anhydride and 260 ml of chloroform were added thereto and stirred for 1 hour under reflux. The mixture obtained was cooled to room temperature, and thereafter the solvent was distilled off, and then the resultant residue was purified by silica gel column chromatography (mobile phase; toluene:heptane=1:3) to produce as a yellow solid 16 g of 4-bromo-7,12-diphenylbenzo[k]fluoranthene.

Aufarbeitung

  1. customThe mixture obtained
  2. distillationthe solvent was distilled off
  3. addition26 ml of trifluoroacetic anhydride and 260 ml of chloroform were added
  4. stirringstirred for 1 hour
  5. temperatureunder reflux
  6. customThe mixture obtained
  7. temperaturewas cooled to room temperature
  8. distillationthe solvent was distilled off
  9. customthe resultant residue was purified by silica gel column chromatography (mobile phase; toluene:heptane=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-03e769965f464c9e86ad36e1eae50bea
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977869B2

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