تفاعل #68746

معادلة التفاعل

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

المردود 75.5%

ظروف التفاعل

المعالجة

1. 1
   أخرىdegassed toluene (25 ml) under an atmosphere of nitrogen
2. 2
   درجة الحرارةto cool to room temperature
3. 3
   أخرىquenched with water (40 ml)
4. 4
   استخلاصextracted with ethyl acetate (3×30 ml)
5. 5
   غسيلwashed with brine (15 ml)
6. 6
   تجفيفdried over anhydrous magnesium sulfate
7. 7
   ترشيحfiltered
8. 8
   أخرىthe filtrate is evaporated under reduced pressure
9. 9
   أخرىThe residue is purified by column chromatography on silica gel

الإجراء التجريبي

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%).

المصدر