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

HRID 1499977Notes

Reaction equation

HRID 1499977 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:15]2[C:20]([C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:8]3[C:13]=1[CH:12]=[CH:11][CH:10]=[CH:9]3)=[CH:19][CH:18]=[CH:17][CH:16]=2

Participants

5

Reactant 3

HCID 117669-PhenylanthraceneHCID 24408BromineHCID 24477Sodium Thiosulfate

Product 1

HCID 41558369-Bromo-10-phenyl-anthraceneYield 89%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

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 delivered dropwise into that reaction solution by a dropping funnel. After the dropping was complete, the mixture was stirred for 1 hour at room temperature. After the reaction, a sodium thiosulfate solution was added to stop the reaction. An organic layer was washed with a NaOH solution and a saturated saline solution, and dried with magnesium sulfate. After natural filtration, concentration and dissolving in toluene were conducted. Then, filtration was done through Florisil, Celite and alumina. The filtrate was concentrated, then recrystallized with dichloromethane and hexane. The target substance, 9-bromo-10-phenylanthracene, was obtained in the form of a pale yellow solid, weighing 7.0 g in a yield of 89% (synthesis scheme (j-4)).

Workup

  1. customwas delivered dropwise into that reaction solution by a dropping funnel
  2. customAfter the reaction
  3. customthe reaction
  4. washAn organic layer was washed with a NaOH solution
  5. dry with materiala saturated saline solution, and dried with magnesium sulfate
  6. filtrationAfter natural filtration, concentration
  7. dissolutiondissolving in toluene
  8. filtrationThen, filtration
  9. concentrationThe filtrate was concentrated
  10. customrecrystallized with dichloromethane and hexane

Sources & evidence

ORD record
ord-83890c7326da4e298f9958d8a9e3b93f
Source dataset
uspto-grants-2015_12
Patent number
US09203035B2

Reaction notes

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