Sodium Carbonate → 2'-Methoxy-biphenyl-4-carboxylic acid ethyl ester

Temperatur

100 °C

A mixture of 4-bromo benzoic acid ethyl ester (2.7 mL, 16.5 mmol), 2-methoxy boronic acid (2.5 g, 16.5 mmol) and sodium carbonate (7.7 g, 72.6 mmol) in toluene:ethanol:water (75 mL:37 mL:37 mL), was flushed with nitrogen for 1 hour. After addition of the tetrakis (triphenylphosphine)palladium (0) catalyst (0.96 g, 0.83 mmol), the reaction mixture was heated at 100° C. overnight. After cooling, the mixture was filtered through Celite which was then rinsed with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a brown oil. Purification of the residue by flash chromatography with a solvent gradient from 25% to 50% dichloromethane in hexane provided the title compound (3.8 g, 89.9%) as a pale yellow oil.

1. customethanol:water (75 mL:37 mL:37 mL), was flushed with nitrogen for 1 hour
2. temperatureAfter cooling
3. filtrationthe mixture was filtered through Celite which
4. washwas then rinsed with ethyl acetate
5. washThe organic layer was washed with water
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give a brown oil
10. customPurification of the residue by flash chromatography with a solvent gradient from 25% to 50% dichloromethane in hexane

ORD-Eintrag

ord-db33cb54316748e58317a9d12fab4c9f

Quelldatensatz

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06903091B2