تفاعل #9370

معادلة التفاعل

2-Bromo-3-ethoxy-cyclopent-2-enone

K2CO3

4-fluorophenylboronic acid

→

3-ethoxy-2-(4-fluoro-phenyl)-cyclopent-2-enone

المردود 70.0%

المذيبات

toluene

benzene

H2O

EtOH

ظروف التفاعل

المعالجة

1. 1
   أخرىthe mixture was purged with N2 for 15 m
2. 2
   workup.ADDITIONThe mixture was diluted with water and EtOAc
3. 3
   استخلاصAfter extracting with EtOAc
4. 4
   تجفيفhexane, the combined organic layers were dried over MgSO4
5. 5
   ترشيحfiltered
6. 6
   أخرىevaporated to dryness
7. 7
   أخرىThe crude oil was purified by column chromatography on silica gel with 2.5% EtOAc

الإجراء التجريبي

2-Bromo-3-ethoxy-cyclopent-2-enone (Intermediate NINE2) (10.5 g, 51.2 mmol) and K2CO3 (14.2 g, 102 mmol) in toluene (100 mL), benzene (100 mL) and H2O (50 mL) was treated with a solution of 4-fluorophenylboronic acid (9.31 g, 66.5) in EtOH (100 mL). Tetrakis(triphenylphosphine)palladium(0) Pd(PPh3)4 (3 g, 2.6 mmol), bis(dibenzylideneacetone)palladium(0), Pd2(dba)3 (0.47 g, 0.5 mmol) and triphenylphosphine (0.27 g, 1.0 mmol) were added and the mixture was purged with N2 for 15 m. The mixture was heated to 100° C. for 15 h. The mixture was diluted with water and EtOAc:hexane. After extracting with EtOAc:hexane, the combined organic layers were dried over MgSO4, filtered and evaporated to dryness. The crude oil was purified by column chromatography on silica gel with 2.5% EtOAc:CH2Cl2 to give 3-ethoxy-2-(4-fluoro-phenyl)-cyclopent-2-enone (Intermediate NINE3) 7.85 g (70%).

المصدر