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温度

0 °C

A solution of 2-fluoro-5-methoxy-4-nitrobenzoic acid (Compound 130E, 1.60 g, 7.44 mmol) in THF (23.6 mL) is slowly charged with sodium borohydride (0.633 g, 16.8 mmol) and stirred for 5 minutes. A solution of boron trifluoride, ethyl ether complex (0.895 mL, 7.26 mmol) in THF (7.85 mL) is added to the reaction mixture. The resulting solution is heated at reflux for 4 h. The reaction mixture was cooled to 0° C., then quenched with ice (15 mL) and diluted with ether (25 mL) and 2 N NaOH (10 mL). The ether layer was washed with brine (15 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield an off-white solid, 1.45 g (97% yield). This material was used without any further purification. 1H NMR (CDCl3, 400 MHz): δ=3.99 (s, 3H), 4.86 (s, 2H), 7.29 (d, J=5.81 Hz, 1H), 7.64 (d, J=9.09 Hz, 1H). MS (ES+): m/z 202.05 [MH+] (TOF, polar).

1. temperatureThe resulting solution is heated
2. temperatureat reflux for 4 h
3. customquenched with ice (15 mL)
4. additiondiluted with ether (25 mL) and 2 N NaOH (10 mL)
5. washThe ether layer was washed with brine (15 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customto yield an off-white solid, 1.45 g (97% yield)
10. customThis material was used without any further purification