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

HRID 546650

Reaction equation

HRID 546650 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 87.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

20.8 g (81.7 mmol) of 9-phenylanthracene and 300 mL of carbon tetrachloride were put into a 500 mL three-necked flask. A solution obtained by dissolving 13.1 g (81.7 mmol) of bromine in 5.00 mL of carbon tetrachloride was dropped into the mixture. After the dropping was completed, the reaction solution was stirred at room temperature for 3 hours to be reacted. Then, about 100 mL of a sodium thiosulfate solution was added to the reaction solution to complete the reaction. An organic layer of the mixture was washed with water and dried over magnesium sulfate. After the drying, the mixture was subjected to suction filtration, and the filtrate was condensed to obtain a solid. The obtained solid was recrystallized by a mixed solvent of chloroform and hexane; then 23.8 g of objective 9-bromo-10-phenylanthracene was obtained as a light yellow powdered solid in a yield of 71%. A synthetic scheme of 9-bromo-10-phenylanthracene is illustrated below (synthetic scheme b-2).

Workup

  1. customA solution obtained
  2. additionwas dropped into the mixture
  3. customto be reacted
  4. customthe reaction
  5. washAn organic layer of the mixture was washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter the drying, the mixture was subjected to suction filtration
  8. customcondensed
  9. customto obtain a solid
  10. customThe obtained solid was recrystallized by a mixed solvent of chloroform and hexane

Sources & evidence

ORD record
ord-f9f67f0bbb5f49fcbd76d2eeafebd004
Source dataset
uspto-grants-2011_05
Patent number
US07935854B2

Linked notes

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