2,6-Dibromoanthraquinone → 2,6-Dibromo-9,10-diphenylanthracene

HRID 240215Notes

Reaction equation

[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:8][C:9]1[CH:22]=[CH:21][C:20]2[C:19](=O)[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Br:24])[CH:17]=3)[C:12](=O)[C:11]=2[CH:10]=1>CCOCC.CC(O)=O>[Br:8][C:9]1[CH:22]=[CH:21][C:20]2[C:11](=[C:12]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:13]3[C:18]([C:19]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:17][C:16]([Br:24])=[CH:15][CH:14]=3)[CH:10]=1

Participants

Conditions

Temperature: 130 °C

Procedure

6 g of phenyl lithium was dissolved in Et2O, and the resulting solution was gradually added dropwise to a solution containing 5 g of 2,6-dibromoanthraquinone dissolved in Et2O. This reaction was carried out on a dry ice bath. Then, the temperature of the reaction material was elevated to room temperature, thereby obtaining white solids. The obtained solids were dissolved in 100 mL of AcOH, followed by addition of KI and NaH2PO2 and the resulting mixture was stirred at 130° C. for 24 hours. After the reaction was complete, the resulting material was filtered with addition of water. The filtrate was then recrystallized from MC and MeOH, thereby obtaining 4.5 g of 2,6-dibromo-9,10-diphenylanthracene.

Workup

additionthe resulting solution was gradually added dropwise to a solution
customThis reaction was carried out on a dry ice bath
customwas elevated to room temperature
customobtaining white solids
filtrationthe resulting material was filtered with addition of water
customThe filtrate was then recrystallized from MC and MeOH

Sources & evidence

ORD record: ord-7918b93899364f3f9e5155c1d11dcbe8
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08647753B2

Reaction notes

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