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

HRID 1012678Notes

Reaction equation

HRID 1012678 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 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.

Workup

  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)

Sources & evidence

ORD record
ord-03e769965f464c9e86ad36e1eae50bea
Source dataset
uspto-grants-2011_07
Patent number
US07977869B2

Reaction notes

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