Reacción #68746

Ecuación de reacción

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

Rendimiento 75.5%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrodegassed toluene (25 ml) under an atmosphere of nitrogen
2. 2
   Temperaturato cool to room temperature
3. 3
   Otroquenched with water (40 ml)
4. 4
   Extracciónextracted with ethyl acetate (3×30 ml)
5. 5
   Lavadowashed with brine (15 ml)
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Otrothe filtrate is evaporated under reduced pressure
9. 9
   OtroThe residue is purified by column chromatography on silica gel

Procedimiento

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%).

Fuente