反应详情

温度

60 °C

To a 250 mL flask equipped with a nitrogen purge, mechanical stirrer, thermometer, condenser and gas scrubber was added 100 mL of perchloroethylene and 16 g (0.12 moles) of AlCl3. The slurry was heated to 60° C. and a solution of 20.4 g (0.10 moles) of 4-(2-fluorophenoxy)phenol in 100 mL of perchloroethylene was added slowly. During the addition HCl gas was given off as the complex with AlCl3 formed. At the end of the addition the temperature was 75° C. The clear, rose-colored solution was cooled to 13° C. with an ice-water bath. To the cooled, rapidly stirred solution was added a total of 16 g (0.1 moles) of liquid bromine dropwise over a 1 hour period at 12°-16° C. After stirring for an additional 30 min, 80 mL of water and 50 mL of methylene chloride were added and the layers were separated. The organic phase was further extracted with 2-50 mL portions of 10% aqueous HCl and then 2-50 mL portions of water. Stripping the solvent under vacuum gave 27.9 g (98.5%) yield of crude product. This crude product was recrystallized from 20 mL of perchloroethylene to give after precipitation, filtration, and drying, 24.2 g (88% yield) of 4-(4-bromo-2-fluorophenoxy)phenol, mp 81-83.5. The identity to the product was confirmed by C13NMR, IR and mixed mp with an authentic sample.

1. customTo a 250 mL flask equipped with a nitrogen
2. custompurge
3. customformed
4. additionAt the end of the addition the temperature
5. customwas 75° C
6. temperatureThe clear, rose-colored solution was cooled to 13° C. with an ice-water bath
7. customthe layers were separated
8. extractionThe organic phase was further extracted with 2-50 mL portions of 10% aqueous HCl
9. customgave 27.9 g (98.5%) yield of crude product
10. customThis crude product was recrystallized from 20 mL of perchloroethylene
11. customto give
12. customafter precipitation, filtration
13. customdrying