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

HRID 919180Notes

Reaction equation

HRID 919180 reaction equation
[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

Participants

4

Reactant 2

HCID 216491,3-DiphenylisobenzofuranHCID 122444035-Bromoacenaphthylene

Product 1

HCID 107909823-Bromo-7,12-diphenylbenzo[k]fluorantheneYield 74.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-739d09d02b624b4cbf1f7330d265667b
Source dataset
uspto-grants-2016_03
Patent number
US09273002B2

Reaction notes

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