Reacción #2030163

ord-99fed4c2c183480e86dca7e96e9a731b

Ecuación de reacción

c1ccc(-c2c3ccccc3cc3ccccc23)cc1
9-phenylanthracene
BrBr
bromine
O=S([O-])([O-])=S.[Na+].[Na+]
sodium thiosulfate
Brc1c2ccccc2c(-c2ccccc2)c2ccccc12
10-bromo-9-phenylanthracene

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrowas dripped through a dropping funnel into the reaction solution
  2. 2
    OtroAfter the reaction
  3. 3
    Otrothe reaction
  4. 4
    LavadoAn organic layer was washed with a sodium hydroxide (NaOH) aqueous solution
  5. 5
    Secadoa saturated saline solution and dried with magnesium sulfate
  6. 6
    FiltraciónAfter the solution was filtered naturally
  7. 7
    Concentraciónthe filtrate was concentrated
  8. 8
    workup.DISSOLUTIONdissolved in toluene
  9. 9
    Filtraciónfiltered through Florisil, Celite, and alumina
  10. 10
    ConcentraciónWhen the filtrate was concentrated
  11. 11
    Otrorecrystallized with dichloromethane and hexane, 7.0 g of a light yellow solid of 10-bromo-9-phenylanthracene that
  12. 12
    Otrowas obtained (yield: 89%)

Procedimiento

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%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08389735B2uspto-grants-2013_03