反应详情

A mixture of phenylboronic acid (1.000 g, 8.20 mmol), methyl 3-bromophenylacetate (1.691 g, 7.38 mmol), Na2CO3 (1.738 g, 16.4 mmol), tetrakis(triphenylphosphine)palladium(0) (0.474 g, 0.41 mmol), toluene (30 mL), and water (5 mL) was heated under reflux for 20 h. The reaction mixture was diluted with water (20 mL) and the volatiles were removed in vacuo. The aqueous solution was washed with EtOAc (4×20 mL). The organic solutions were combined, washed with 1N NaOH (15 mL) followed by water (15 mL). The organic solution was dried (MgSO4), filtered and concentrated in vacuo. Purification by medium pressure chromatography (79:1 hexanes:EtOAc to 39:1 hexanes:EtOAc) provided biphenyl-3-yl-acetic acid methyl ester (1.316 g).

1. temperaturewas heated
2. temperatureunder reflux for 20 h
3. customthe volatiles were removed in vacuo
4. washThe aqueous solution was washed with EtOAc (4×20 mL)
5. washwashed with 1N NaOH (15 mL)
6. dry with materialThe organic solution was dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customPurification by medium pressure chromatography (79:1 hexanes:EtOAc to 39:1 hexanes:EtOAc)