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

HRID 1926179Notes

Reaction equation

HRID 1926179 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-anthraceneYield 99.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

6.0 g (23.7 mmol) of 9-phenylanthracene was dissolved into 80 mL of carbon tetrachloride, and a solution in which 3.80 g (21.1 mmol) of bromine was dissolved in 10 mL of carbon tetrachloride was dropped into the reaction solution using a dropping funnel. After dropping, the solution was stirred for 1 hour at a room temperature. After the reaction, an aqueous sodium thiosulfate solution was added to stop the reaction. An organic layer was washed with an aqueous sodium hydroxide (NaOH) solution and a saturated sodium chloride solution and dried with magnesium sulfate. The mixture was naturally filtered, and a compound obtained by concentrating the filtrate was dissolved into toluene and filtered through florisil, Celite®, and alumina. The filtrate was concentrated and recrystallized with dichloromethane and hexane, thereby obtaining 7.0 g of objective 10-bromo-9-phenylanthracene as a light-yellow solid with a yield of 89%.

Workup

  1. additionwas dropped into the reaction solution
  2. customAfter the reaction
  3. customthe reaction
  4. washAn organic layer was washed with an aqueous sodium hydroxide (NaOH) solution
  5. dry with materiala saturated sodium chloride solution and dried with magnesium sulfate
  6. filtrationThe mixture was naturally filtered
  7. customa compound obtained
  8. concentrationby concentrating the filtrate
  9. dissolutionwas dissolved into toluene
  10. filtrationfiltered through florisil, Celite®, and alumina
  11. concentrationThe filtrate was concentrated
  12. customrecrystallized with dichloromethane and hexane

Sources & evidence

ORD record
ord-50a6b6f545804828b34cd281633ef2f1
Source dataset
uspto-grants-2012_05
Patent number
US08178885B2

Reaction notes

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