反应详情

4-Fluro-3-nitrotoluene (7.5 g, 48.4 mmol) is treated with a solution of nitroethane (15.2 mL, 200 mmol) in ethyl acetate (100 mL) and DBU (21 mL, 145 mmol) and stirred overnight at ambient temperature. The solution is concentrated under vacuum, diluted with methanol, treated with 30% H2O2 (25 mL) and 10% sodium bicarbonate (25 ml) and stirred overnight at ambient temperature. The reaction mixture is concentrated in vacuo, acidified with 5% HCl and extracted with methylene chloride. The organic layer is dried (sodium sulfate) and chromatographed (35% ethyl acetate/hexane) to give the title compound (7.2 g, 40.2 mmol). MS m/z: M+=279; 1H NMR (CDCl3, 300 MHz) δ7.8 (s, 1H), 7.48 (d, 1H), 7.32 (d, 1H), 2.5 (s, 3H), 2.4 (s, 3H).

1. concentrationThe solution is concentrated under vacuum
2. additiondiluted with methanol
3. additiontreated with 30% H2O2 (25 mL) and 10% sodium bicarbonate (25 ml)
4. stirringstirred overnight at ambient temperature
5. concentrationThe reaction mixture is concentrated in vacuo
6. extractionextracted with methylene chloride
7. dry with materialThe organic layer is dried (sodium sulfate)
8. customchromatographed (35% ethyl acetate/hexane)