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

HRID 2360744Notes

Reaction equation

HRID 2360744 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 dripped through a dropping funnel into the reaction solution. After the dripping, 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 a saturated saline solution 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 that was an object was obtained (yield: 89%).

Workup

  1. customwas dripped 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
  5. dry with materiala saturated saline solution and dried 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 that
  12. customwas obtained (yield: 89%)

Sources & evidence

ORD record
ord-c15033fb9852448ca0ea1e3c99d25cd0
Source dataset
uspto-grants-2014_04
Patent number
US08686159B2

Reaction notes

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