反应详情

温度

-78 °C

To a stirring solution of (5-cyano-4-fluoro-2-methoxy-N-(3-nitro-benzyl)-benzamide (1.5 g, 4.6 mmol) in dichloromethane (200 mL, 0.3 M) at −78° C. was added BBr3 (21.5 mL, 21.4 mmol). The mixture was allowed to stir for 45 min at −78° C. and the dry ice/acetone bath was then removed and tje solution was allowed to warm to room temperature. Then, the solution was cooled down again to −78° C. and was then quenched with 100 mL of methanol. The mixture was allowed to warm to room temperature and concentrated. Purification by MPLC (10–100% ethyl acetate, 23 mL/min, 75 min) provided 5-cyano-4-fluoro-2-hydroxy-N-(3-nitro-benzyl)-benzamide (0.85 g, 59%) as a beige powder: Rf 0.37 (70% ethyl acetate in heptane); 1H NMR (DMSO-d6, 300 MHz) δ 9.50 (bd s, 1 H), 8.39 (d, J=7.5 Hz, 1 H;), 8.20 (s, 1 H), 8.12 (d, J=9.3 Hz, 1 H), 7.80 (d, J=7.2 Hz, 1H), 7.63 (t, J=7.8 Hz, 1 H), 7.04 (d, J=11.1 Hz, 1 H), 4.62 (s, 2H).

1. customthe dry ice/acetone bath was then removed
2. temperatureto warm to room temperature
3. temperatureThen, the solution was cooled down again to −78° C.
4. customwas then quenched with 100 mL of methanol
5. temperatureto warm to room temperature
6. concentrationconcentrated
7. customPurification by MPLC (10–100% ethyl acetate, 23 mL/min, 75 min)