反应详情

温度

90 °C

A mixture of 3,6-dichloropyridazine (1.0 g, 5.23 mmol), phenol (0.50 g, 5.31 mmol), potassium carbonate (2.90 g, 20.98 mmol), and copper(I) iodide (0.59 g, 3.09 mmol) in dimethylsulfoxide (3.6 mL, 1.45 M) was heated to 90° C. overnight. After this time, the reaction was cooled to 25° C. and then poured into a 2N aqueous hydrochloric acid solution (75 mL) rinsing with water. The resulting mixture was filtered through filter paper and diluted with a saturated aqueous sodium chloride solution followed by extraction with ethyl acetate (150 mL). The organics were washed with a saturated aqueous sodium chloride solution (1×75 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel column chromatography (AnaLogix, 80 g, 5-24% ethyl acetate/hexanes) afforded 3-chloro-6-phenoxy-pyridazine (1.01 g, 93%) as a yellow solid. 1H-NMR (300 MHz, DMSO-d6) δ ppm 7.14-7.35 (m, 3H), 7.47 (t, J=7.5 Hz, 2H), 7.59 (d, J=9.2 Hz, 1H), 7.96 (d, J=9.2 Hz, 1H).

1. temperatureAfter this time, the reaction was cooled to 25° C.
2. washrinsing with water
3. filtrationThe resulting mixture was filtered
4. filtrationthrough filter paper
5. additiondiluted with a saturated aqueous sodium chloride solution
6. extractionfollowed by extraction with ethyl acetate (150 mL)
7. washThe organics were washed with a saturated aqueous sodium chloride solution (1×75 mL)
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo