반응 #9370

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

K2CO3

4-fluorophenylboronic acid

→

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

수율 70.0%

용매

toluene

benzene

H2O

EtOH

반응 조건

후처리

1. 1
   기타the mixture was purged with N2 for 15 m
2. 2
   workup.ADDITIONThe mixture was diluted with water and EtOAc
3. 3
   추출After extracting with EtOAc
4. 4
   건조hexane, the combined organic layers were dried over MgSO4
5. 5
   여과filtered
6. 6
   기타evaporated to dryness
7. 7
   기타The crude oil was purified by column chromatography on silica gel with 2.5% EtOAc

실험 절차

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%).

출처