Реакция #68746

Уравнение реакции

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

Выход 75.5%

Условия реакции

Обработка

1. 1
   Другоеdegassed toluene (25 ml) under an atmosphere of nitrogen
2. 2
   Температураto cool to room temperature
3. 3
   Другоеquenched with water (40 ml)
4. 4
   Экстракцияextracted with ethyl acetate (3×30 ml)
5. 5
   Промывкаwashed with brine (15 ml)
6. 6
   Сушкаdried over anhydrous magnesium sulfate
7. 7
   Фильтрацияfiltered
8. 8
   Другоеthe filtrate is evaporated under reduced pressure
9. 9
   ДругоеThe residue is purified by column chromatography on silica gel

Методика

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%).

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