9-Phenylanthracene → 9-Bromo-10-phenyl-anthracene

HRID 2075611Notes

Reaction equation

HRID 2075611 reaction equation
[C:1]1([C:7]2[C:8]3[C:13]([CH:14]=[C:15]4[C:20]=2[CH:19]=[CH:18][CH:17]=[CH:16]4)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:21]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:21][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[CH:19]2

Participants

5

Reactant 3

HCID 117669-PhenylanthraceneHCID 24408BromineHCID 24477Sodium Thiosulfate

Product 1

HCID 41558369-Bromo-10-phenyl-anthracene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

After 6.0 g (23.7 mmol) of 9-phenylanthracene was dissolved in 80 mL of carbon tetrachloride, a solution of 3.80 g (21.1 mmol) of bromine dissolved in 10 mL of carbon tetrachloride was dropped through a dropping funnel into the reaction solution. After the dropping, the solution was stirred at room temperature for one hour After the reaction, a sodium thiosulfate aqueous solution was added to stop the reaction. An organic layer was washed with a sodium hydroxide (NaOH) aqueous solution and saturated saline and dried with magnesium sulfate. After the solution was filtered naturally, the filtrate was concentrated, dissolved in toluene, and filtered through Florisil, Celite, and alumina. When the filtrate was concentrated and recrystallized with dichloromethane and hexane, 7.0 g of a light-yellow solid of 10-bromo-9-phenylanthracene, which is a target matter, was obtained with a yield of 89%.

Workup

  1. additionwas dropped through a dropping funnel into the reaction solution
  2. customAfter the reaction
  3. customthe reaction
  4. washAn organic layer was washed with a sodium hydroxide (NaOH) aqueous solution and saturated saline
  5. dry with materialdried with magnesium sulfate
  6. filtrationAfter the solution was filtered naturally
  7. concentrationthe filtrate was concentrated
  8. dissolutiondissolved in toluene
  9. filtrationfiltered through Florisil, Celite, and alumina
  10. concentrationWhen the filtrate was concentrated
  11. customrecrystallized with dichloromethane and hexane, 7.0 g of a light-yellow solid of 10-bromo-9-phenylanthracene, which
  12. customwas obtained with a yield of 89%

Sources & evidence

ORD record
ord-0080101779af45f1b1b609442ef7f525
Source dataset
uspto-grants-2011_04
Patent number
US07919773B2

Reaction notes

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