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Benzene → 9,10-Diphenylanthracene

HRID 413558
Notes
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Reaction equation

HRID 413558 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9](Br)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:23]1(OB(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.OO>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[C:17]1([C:2]2[C:3]3[C:8]([C:9]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:10]4[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 241BenzeneHCID 784Hydrogen PeroxideHCID 682269,10-DibromoanthraceneHCID 78412Phenyl dihydrogen orthoborate

Product 1

HCID 151599,10-DiphenylanthraceneYield 75.5%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent

Procedure

To a mixed solution of 286.6 g (0.85 mol) of 9,10-dibromoanthracene, 29.9 g (0.0255 mol) of Pd(PPh3)4 and 3L of benzene was added 1.5L of 2M Na2CO3aq and 1.2 L of ethanol solution of 228.6 g (1.87 mol) of phenyl boric acid, followed by refluxing for 6 hours. To the reaction solution was added 200 mL of 30% H2O2 to terminate the reaction, and an organic layer was recovered. The organic layer was washed with water and dehydrated by anhydrous magnesium sulfate, followed by filtration and concentration of the filtrate to 750 mL in total. The precipitated crystal was filtered and dried to give 212.0 g of 9,10-diphenylanthracene (Yield 75.5%, HPLC purity 97.6%).

Workup

  1. temperatureby refluxing for 6 hours
  2. customto terminate
  3. customthe reaction
  4. customan organic layer was recovered
  5. washThe organic layer was washed with water
  6. filtrationfollowed by filtration and concentration of the filtrate to 750 mL in total
  7. filtrationThe precipitated crystal was filtered
  8. customdried

Sources & evidence

ORD record
ord-53d532414f0946da9b60d3647a6c3045
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06566572B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes