반응 #68746

반응 방정식

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

수율 75.5%

반응 조건

후처리

1. 1
   기타degassed toluene (25 ml) under an atmosphere of nitrogen
2. 2
   온도to cool to room temperature
3. 3
   기타quenched with water (40 ml)
4. 4
   추출extracted with ethyl acetate (3×30 ml)
5. 5
   세척washed with brine (15 ml)
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   여과filtered
8. 8
   기타the filtrate is evaporated under reduced pressure
9. 9
   기타The residue is purified by column chromatography on silica gel

실험 절차

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%).

출처