反应详情

温度

75 °C

To a mixture of 3-chloro-5-fluoro-4-nitrophenol (2.6 g, 13 mmol), cesium carbonate (8.7 g, 27 mmol), and 2-(chloromethyl)-5-methylpyridine hydrochloride (2.4 g, 13 mmol) was added DMF (88 mL) and the resulting mixture was heated to 75° Celsius for 19 h. The mixture was cooled to RT and then stirred for an additional 20 h. The resulting mixture was then partitioned between sat. NaHCO3 and EtOAc. The organic layer was separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated to dryness. The resulting residue was purified using FCC to afford the title compound (2.93 g, 74%). MS (ESI): mass calcd. for C13H10ClFN2O3, 296.04; m/z found, 297.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.45 (dd, J=1.4, 0.7, 1H), 7.55 (dd, J=7.9, 1.6, 1H), 7.32 (d, J=7.9, 1H), 6.93 (dd, J=2.5, 1.8, 1H), 6.79 (dd, J=11.1, 2.6, 1H), 5.19 (s, 2H), 2.37 (s, 3H).

1. temperatureThe mixture was cooled to RT
2. customThe resulting mixture was then partitioned between sat. NaHCO3 and EtOAc
3. customThe organic layer was separated
4. extractionthe aqueous layer was further extracted with EtOAc
5. washThe combined organic layers were washed with brine
6. customdried
7. concentrationconcentrated to dryness
8. customThe resulting residue was purified