反应 #1509644

反应方程式

SnCl2

phenyllithium

2,6-dibromoanthraquinone

HCl

HCl

→

2,6-dibromo-9,10-diphenylanthracene

溶剂

THF

THF

反应条件

后处理

1. 1
   其他to come to RT
2. 2
   其他the mixture is partitioned between toluene and water
3. 3
   干燥the organic phase is dried over Na2SO4
4. 4
   其他the solvent is removed in vacuo
5. 5
   workup.WAITthe mixture is brought to an internal temperature of 140° C. for 2 h
6. 6
   过滤the precipitate is filtered off with suction
7. 7
   洗涤washed with water, EtOH and ethyl acetate
8. 8
   其他dried at 80° C. in vacuo
9. 9
   其他Recrystallisation from toluene
10. 10
    其他gives 30.8 g (63 mmol, 63%) of an ochre solid, which
11. 11
    其他1H-NMR and is employed in this form in the subsequent reaction

实验过程

36.6 g (100 mmol) of 2,6-dibromoanthraquinone are dissolved in 600 ml of THF, the solution is cooled to −75° C., and 100 ml of a 2 M phenyllithium solution in THF are added dropwise. After 2 h, the mixture is allowed to come to RT, 50 ml of 4 M HCl are added, the mixture is partitioned between toluene and water, the organic phase is dried over Na2SO4, and the solvent is removed in vacuo. The residue is taken up in 350 ml of DMF, 68 g (350 mmol) of SnCl2 are added, and the mixture is brought to an internal temperature of 140° C. for 2 h. 180 ml of 2 M HCl are then added at about 40° C., and the precipitate is filtered off with suction, washed with water, EtOH and ethyl acetate and dried at 80° C. in vacuo. Recrystallisation from toluene gives 30.8 g (63 mmol, 63%) of an ochre solid, which is homogeneous according to TLC and 1H-NMR and is employed in this form in the subsequent reaction.

来源