反应详情

温度

100 °C

A mixture of 3-methyl-4-bromobenzoic acid methyl ester (2.0 g, 8.7 mmol), 2-methoxyphenyl boronic acid (1.32 g, 8.7 mmol) and sodium carbonate (4.1 g, 38.7 mmol) in toluene:ethanol:water (50 mL:25 mL: 25 mL) was purged with nitrogen for 1 hour. After addition of the tetrakis(triphenylphosphine) palladium(0) catalyst (0.50 g, 0.43 mmol), the reaction mixture was heated at 100° C. overnight. After cooling, the reaction was filtered through Celite® and the cake washed 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 by flash chromatography on silica gel with a solvent gradient from 20% to 50% dichloromethane in hexane gave 2.0 g of product as a colorless oil. MS [(+)APCI, m/z]: 257 [M+H]+. Anal. Calcd. for C16H16O3: C, 74.98; H, 6.29. Found: C, 74.06; H, 6.17.

1. customethanol:water (50 mL:25 mL: 25 mL) was purged with nitrogen for 1 hour
2. temperatureAfter cooling
3. filtrationthe reaction was filtered through Celite®
4. washthe cake washed 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 by flash chromatography on silica gel with a solvent gradient from 20% to 50% dichloromethane in hexane