反应详情

温度

145 °C

To a flask charged with 4-bromo-2-chloro-3-(hydroxymethyl)phenol (2.44 g, 10.3 mmol) and a stir bar was added CuCN (2.76 g, 30.8 mmol) and DMF (25 mL). The flask was fitted with a condenser and purged three times with Nitrogen. The solution was then heated to 145° C. for 2 hours. At that point, water (0.555 mL, 30.8 mmol) was added to the reaction via a syringe, and the reaction was kept at 100° C. for another 24 hours. The reaction was cooled to RT, diluted with DCM (100 mL), and filtered through a pad of celite to remove the solids. The filtrate was washed with saturated NH4OAc, dried over sodium sulfate, concentrated and purified by silica gel flash chromatography. 4-Chloro-5-hydroxy-2-benzofuran-1(3H)-one was collected after removal of solvents. 1H-NMR (500 MHz, CDCl3) δ ppm 9.13 (broad, 1H), 7.68 (d, J=8.5 Hz, 1H), 7.19 (d, J=8.5 Hz, 1H), 5.23 (s, 2H).

1. customThe flask was fitted with a condenser
2. custompurged three times with Nitrogen
3. temperatureThe reaction was cooled to RT
4. filtrationfiltered through a pad of celite
5. customto remove the solids
6. washThe filtrate was washed with saturated NH4OAc
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated
9. custompurified by silica gel flash chromatography
10. custom4-Chloro-5-hydroxy-2-benzofuran-1(3H)-one was collected
11. customafter removal of solvents