反应详情

温度

110 °C

To a flame dried flask containing degassed toluene (15.2 mL, 0.5 M) was added 5-bromo-4-fluoro-2-methoxy-benzoic acid methyl ester (2.0 g, 7.6 mmol), anhydrous K2CO3 (2.1 g, 15.2 mmol), phenylboronic acid (3.7 g, 30.4 mmol), and Pd(PPh3)4 (0.88 g, 0.76 mmol). Using a reflux condenser, the stirring mixture was heated to 110° C. for 3.5 h. The mixture was then cooled to room temperature, placed in an ice bath and H2O2 (30%, 10 mL) was slowly added. The ice bath was removed and the reaction was allowed to stir at room temperature for one hour. The mixture was then diluted with ether and washed successively with 2 N HCl and saturated aq NaCl. The organic layer was dried over Na2SO4, filtered, and concentrated to afford a brown oil. Purification by MPLC (10–100% ethyl acetate in heptane, 23 mL/min, 75 min) provided 6-fluoro-4-methoxy-biphenyl-3-carboxylic acid methyl ester (1.8 g, 91%) as a pale yellow solid: Rf 0.5 (40% ethyl acetate in heptane);

1. customTo a flame dried flask
2. additioncontaining
3. customdegassed toluene (15.2 mL, 0.5 M)
4. temperatureThe mixture was then cooled to room temperature
5. customplaced in an ice bath
6. customThe ice bath was removed
7. additionThe mixture was then diluted with ether
8. washwashed successively with 2 N HCl and saturated aq NaCl
9. dry with materialThe organic layer was dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. customto afford a brown oil
13. customPurification by MPLC (10–100% ethyl acetate in heptane, 23 mL/min, 75 min)