反应 #52142

反应方程式

(2-iodo-3,4,5-trimethoxyphenyl) diphenylphosphine oxide

(2-iodo-3,4,5-trimethoxyphenyl)diphenylphosphine oxide

phenylboronic acid

→

product 22

收率 98.0%

(2-phenyl-3,4,5-trimethoxyphenyl)diphenylphosphine oxide

收率 98.0%

反应条件

后处理

1. 1
   其他degassed THF (800 ml)
2. 2
   workup.ADDITIONA solution of degassed saturated K2CO3 (400 ml) was added afterwards
3. 3
   其他The whole mixture was degassed with nitrogen for an additional 10 min
4. 4
   温度at reflux under nitrogen for 24 hrs
5. 5
   浓缩The reaction mixture was concentrated under reduced pressure
6. 6
   其他to remove THF and 400 ml of CH2Cl2
7. 7
   workup.ADDITIONwas then added
8. 8
   洗涤The CH2Cl2 layer was washed with water (200 ml) and brine (200 ml)
9. 9
   干燥dried over Na2SO4
10. 10
    其他evaporated
11. 11
    其他The solid residue was recrystallized from EtOAc (100 ml)

实验过程

To a 2 liter Schlenk flask was added (2-iodo-3,4,5-trimethoxyphenyl) diphenylphosphine oxide 21 (30 g, 61 mmol), phenylboronic acid (11.1 g, 91 mmol), and degassed THF (800 ml). A solution of degassed saturated K2CO3 (400 ml) was added afterwards. The whole mixture was degassed with nitrogen for an additional 10 min. Then, Pd(PPh3)4 (1.22 mmol, 1.4 g) was added in the solution through one portion. The mixture was stirred at reflux under nitrogen for 24 hrs. In situ 31PNMR showed that the reaction was complete. The reaction mixture was concentrated under reduced pressure to remove THF and 400 ml of CH2Cl2 was then added. The CH2Cl2 layer was washed with water (200 ml) and brine (200 ml), dried over Na2SO4, and evaporated. The solid residue was recrystallized from EtOAc (100 ml) to give off-white product 22 (23 g). The mother liquid was passed though a silica gel column to give another 4 g of product 22. The total yield was 98%.

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