2,6-Dibromoanthraquinone → 2,6-Dibromo-9,10-di(naphthalen-1-yl)anthracene

HRID 240216Notes

Reaction equation

HRID 240216 reaction equation
[C:1]1([Li])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:12][C:13]1[CH:26]=[CH:25][C:24]2[C:23](=O)[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([Br:28])[CH:21]=3)[C:16](=O)[C:15]=2[CH:14]=1>CCOCC.CC(O)=O>[Br:12][C:13]1[CH:26]=[CH:25][C:24]2[C:15](=[C:16]([C:9]3[C:10]4[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=4)[CH:6]=[CH:7][CH:8]=3)[C:17]3[C:22]([C:23]=2[C:1]2[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=2)=[CH:21][C:20]([Br:28])=[CH:19][CH:18]=3)[CH:14]=1

Participants

5

Reactant 2

HCID 109594842,6-DibromoanthraquinoneHCID 178506670HCID 178506670, compound

Product 1

HCID 588551262,6-Dibromo-9,10-di(naphthalen-1-yl)anthraceneYield 49.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
130 °C

Procedure

5 g of 1-naphthyl 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 an intermediate product. The obtained intermediate product was filtered, thereby obtaining white solids. The white solids thus obtained were dissolved in 100 mL of AcOH, followed by addition of KI and NaH2PO2 and the mixture was stirred at 130° C. for 24 hours. When the reaction was complete, the reaction material was filtered with addition of water. The filtrate was recrystallized from MC and MeOH, thereby obtaining 4 g of 2,6-dibromo-9,10-di-1-naphthylanthracene.

Workup

  1. additionthe resulting solution was gradually added dropwise to a solution
  2. customThis reaction was carried out on a dry ice bath
  3. customwas elevated to room temperature
  4. customobtaining an intermediate product
  5. filtrationThe obtained intermediate product was filtered
  6. customobtaining white solids
  7. customThe white solids thus obtained
  8. filtrationthe reaction material was filtered with addition of water
  9. customThe filtrate was recrystallized from MC and MeOH

Sources & evidence

ORD record
ord-395eeb53d04744799182f386420a9117
Source dataset
uspto-grants-2014_02
Patent number
US08647753B2

Reaction notes

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