反应 #68746

反应方程式

2-bromo-3-methoxycyclopent-2-enone

4′-chloro-4-ethylbiphen-3-ylboronic acid

potassium phosphate

→

2-(4′-chloro-4-ethylbiphen-3-yl)-3-methoxycyclopent-2-enone

收率 75.5%

反应条件

后处理

1. 1
   其他degassed toluene (25 ml) under an atmosphere of nitrogen
2. 2
   温度to cool to room temperature
3. 3
   其他quenched with water (40 ml)
4. 4
   萃取extracted with ethyl acetate (3×30 ml)
5. 5
   洗涤washed with brine (15 ml)
6. 6
   干燥dried over anhydrous magnesium sulfate
7. 7
   过滤filtered
8. 8
   其他the filtrate is evaporated under reduced pressure
9. 9
   其他The residue is purified by column chromatography on silica gel

实验过程

To a stirred suspension of 2-bromo-3-methoxycyclopent-2-enone (1.0 g, 5.23 mmol), 4′-chloro-4-ethylbiphen-3-ylboronic acid (2.03 g, 7.80 mmol) and potassium phosphate (2.23 g, 10.50 mmol) in anhydrous, degassed toluene (25 ml) under an atmosphere of nitrogen is added palladium(II)acetate (24 mg, 0.105 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (86 mg, 0.209 mmol). The reaction is heated at 90° C. for 4 hours and then allowed to cool to room temperature, quenched with water (40 ml) and extracted with ethyl acetate (3×30 ml). The organic extracts are combined, washed with brine (15 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 2-(4′-chloro-4-ethylbiphen-3-yl)-3-methoxycyclopent-2-enone (1.29 g, 75%).

来源