反应 #1509639

反应方程式

tri-tert-butyl phosphine

Di-p-tolylamine

4,4′-dibromobiphenyl

Sodium tert-butoxide

→

material

收率 3.0%

4′-bromo-N,N-di-p-tolylbiphenyl-4-amine

收率 3.0%

溶剂

—

hexanes

—

hexanes

ethyl acetate

反应条件

后处理

1. 1
   其他was degassed in toluene (anhydrous, 50 mL) for 20 minutes
2. 2
   其他the mixture was further degassed for 15 minutes
3. 3
   其他mixture was further degassed for 10 minutes
4. 4
   温度After cooling
5. 5
   workup.ADDITIONthe mixture was poured into DCM, and solids
6. 6
   过滤were filtered off
7. 7
   洗涤Filtrate was washed with water and brine
8. 8
   其他The organic layer was collected
9. 9
   干燥dried over sodium sulfate

实验过程

A mixture of tris(dibenzylideneacetone)dipalladium (353 mg, 0.385 mmol), and tri-tert-butyl phosphine (3.11 g of a 10% solution in hexanes) was degassed in toluene (anhydrous, 50 mL) for 20 minutes. Di-p-tolylamine (3.00 g, 15.2 mmol), and 4,4′-dibromobiphenyl (4.80 g, 15.4 mmol) were added and the mixture was further degassed for 15 minutes. Sodium tert-butoxide (2.4 g, 25 mmol) was added, and mixture was further degassed for 10 minutes. The whole was heated overnight at 120° C. under argon. After cooling, the mixture was poured into DCM, and solids were filtered off. Filtrate was washed with water and brine. The organic layer was collected and dried over sodium sulfate, then loaded onto silica gel. A flash column (gradient of 2-20% ethyl acetate in hexanes) gave 190 mg of material (3% yield); confirmed pure by HNMR.

来源