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

HRID 1992784Notes

Reaction equation

HRID 1992784 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, and then, in the reaction solution thereof, a solution in which 3.80 g (21-1 mmol) of bromine was dissolved in 10 mL of carbon tetrachloride was dropped by a dropping funnel. After dropping, it was stirred for one hour at room temperature. After reaction, a sodium thiosulfate aqueous solution was added thereto and stirred. An organic layer was washed with a sodium hydroxide aqueous solution and saturated saline, and then dried with magnesium sulfate. After the mixture was subjected to natural filtration, the filtrate was concentrated and dissolved in toluene, and then filtration was carried out using florisil, celite, and alumina. When the filtrate was concentrated and then recrystallized with a mixed solution of dichloromethane and hexane, 7.0 g of 9-bromo-10-phenylanthracene that was a target substance was obtained as a light yellow solid at a yield of 89% (Synthesis scheme (b-2)).

Workup

  1. additionwas dropped by a dropping funnel
  2. customAfter reaction
  3. stirringstirred
  4. washAn organic layer was washed with a sodium hydroxide aqueous solution and saturated saline
  5. dry with materialdried with magnesium sulfate
  6. filtrationAfter the mixture was subjected to natural filtration
  7. concentrationthe filtrate was concentrated
  8. dissolutiondissolved in toluene
  9. filtrationfiltration
  10. concentrationWhen the filtrate was concentrated
  11. customrecrystallized with a mixed solution of dichloromethane and hexane, 7.0 g of 9-bromo-10-phenylanthracene that
  12. customwas obtained as a light yellow solid at a yield of 89% (Synthesis scheme (b-2))

Sources & evidence

ORD record
ord-681826b616a94e5aab91135d5e0e3b3e
Source dataset
uspto-grants-2010_01
Patent number
US07649211B2

Reaction notes

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