Potassium Carbonate → 3-Ethoxy-2-(4-fluoro-phenyl)-cyclopent-2-enone

Temperature

100 °C

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%).

1. customthe mixture was purged with N2 for 15 m
2. additionThe mixture was diluted with water and EtOAc
3. extractionAfter extracting with EtOAc
4. dry with materialhexane, the combined organic layers were dried over MgSO4
5. filtrationfiltered
6. customevaporated to dryness
7. customThe crude oil was purified by column chromatography on silica gel with 2.5% EtOAc

ORD record

ord-1b99ecc263fc43ae8cb7d0f030d361c9

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091232B2