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

HRID 11194Notes

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

Conditions

Temperature: 80 °C

Procedure

5 g (18.5 mmol) of diphenylisobenzofuran and 4.3 g (18.5 mmol) of 5-bromoacenaphthylene in toluene were agitated for 24 hours at the reflux temperature. The solvent was distilled off in vacuum, after which the residue was dissolved in 500 ml of acetic acid. An aqueous 40% hydrobromic acid solution, 50 cm3, was added to the solution, which was heated at 80° C. for one hour. After cooling to room temperature, the precipitate was collected by filtration. This was purified by silica gel chromatography using a mixture of toluene and hexane as an extracting solvent, yielding 7 g of 3-bromo-7,12-diphenylbenzo[k]fluoranthene having a yellowish white color.

Workup

distillationThe solvent was distilled off in vacuum
dissolutionafter which the residue was dissolved in 500 ml of acetic acid
additionAn aqueous 40% hydrobromic acid solution, 50 cm3, was added to the solution, which
temperatureAfter cooling to room temperature
filtrationthe precipitate was collected by filtration
customThis was purified by silica gel chromatography
additiona mixture of toluene and hexane as an extracting solvent

Sources & evidence

ORD record: ord-cda3828502ec4ec5b4a279b75eb3511f
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07097917B1

Reaction notes

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