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

HRID 1806192Notes

Reaction equation

HRID 1806192 reaction equation
[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

Participants

4

Reactant 2

HCID 216491,3-DiphenylisobenzofuranHCID 122444035-Bromoacenaphthylene

Product 1

HCID 107909823-Bromo-7,12-diphenylbenzo[k]fluorantheneYield 52.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

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

Workup

  1. distillationthe solvent was distilled off
  2. additionThen, 26 ml of trifluoroacetic anhydride and 260 ml of chloroform were added
  3. stirringby stirring
  4. temperatureunder reflux for 1 hour
  5. temperatureAfter the mixture was cooled to room temperature
  6. distillationthe solvent was distilled off
  7. customThe obtained residue was purified by silica gel chromatography (mobile phase; toluene:heptane=1:3)

Sources & evidence

ORD record
ord-fcb6199e435446129a53a77834d81844
Source dataset
uspto-grants-2013_01
Patent number
US08354788B2

Reaction notes

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