Reacción #624774

Ecuación de reacción

9-phenylanthracene

bromine

sodium thiosulfate

→

9-bromo-10-phenylanthracene

Rendimiento 89.0%

Disolventes

carbon tetrachloride

carbon tetrachloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas dropped by a dropping funnel
2. 2
   OtroAfter reaction
3. 3
   workup.STIRRINGstirred
4. 4
   LavadoAn organic layer was washed with a sodium hydroxide aqueous solution and saturated saline
5. 5
   Secadodried with magnesium sulfate
6. 6
   FiltraciónAfter the mixture was subjected to natural filtration
7. 7
   Concentraciónthe filtrate was concentrated
8. 8
   workup.DISSOLUTIONdissolved in toluene
9. 9
   Filtraciónfiltration
10. 10
    ConcentraciónWhen the filtrate was concentrated
11. 11
    Otrorecrystallized with a mixed solution of dichloromethane and hexane, 7.0 g of 9-bromo-10-phenylanthracene that
12. 12
    Otrowas obtained as a light yellow solid at a yield of 89% (Synthesis scheme (b-2))

Procedimiento

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)).

Fuente