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

HRID 1928968Notes

Reaction equation

HRID 1928968 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.C1(C)C=CC=CC=1>[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

6

Reactant 3

HCID 117669-PhenylanthraceneHCID 24408BromineHCID 24477Sodium Thiosulfate

Product 1

HCID 41558369-Bromo-10-phenyl-anthracene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 5943Carbon TetrachlorideSolvent2×

Procedure

25.0 g (98.3 mmol) of 9-phenylanthracene was put into a 1-L three-neck flask, and 300 mL of carbon tetrachloride was added thereto. A solution in which 15.6 g (98.3 mmol) of bromine was dissolved in 40 mL of carbon tetrachloride was dropped in the reaction solution at the room temperature. After the dropping, the reaction solution was stirred at the room temperature for 1 hour. Thereafter, the reaction is completed by adding a sodium thiosulfate aqueous solution, and the solution was further stirred for 1 hour. An organic layer of the reaction mixture was washed with aqueous sodium hydroxide (2.0 mol/L) and saturated saline and dried with magnesium sulfate. This mixture was filtrated naturally, and the filtrate was condensed to obtain a solid. The solid was dissolved in toluene, and the solution was subjected to suction filtration through Florisil, celite, and then alumina. The filtrate was concentrated to obtain a solid, and the solid was recrystallized with a mixture solution of dichloromethane and hexane, whereby 27.8 g of a light yellow powdery solid that was a target matter was obtained with the yield of 85%.

Workup

  1. additionwas dropped in the reaction solution at the room temperature
  2. stirringthe solution was further stirred for 1 hour
  3. washAn organic layer of the reaction mixture was washed with aqueous sodium hydroxide (2.0 mol/L) and saturated saline
  4. dry with materialdried with magnesium sulfate
  5. filtrationThis mixture was filtrated naturally
  6. customcondensed
  7. customto obtain a solid
  8. filtrationthe solution was subjected to suction filtration through Florisil, celite
  9. concentrationThe filtrate was concentrated
  10. customto obtain a solid
  11. customthe solid was recrystallized with a mixture solution of dichloromethane and hexane, whereby 27.8 g of a light yellow powdery solid
  12. customwas obtained with the yield of 85%

Sources & evidence

ORD record
ord-b05e134d621c4048906f8102304dc317
Source dataset
uspto-grants-2012_05
Patent number
US08183793B2

Reaction notes

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