反应详情

温度

100 °C

To 2-(4-methylphenyl)oxazole (6.41 g, 40.3 mmol) and N-bromosuccinimide (14.7 g, 82.6 mmol) in carbon tetrachloride (300 mL) was added 2,2′-azobisisobutyronitrile (500 mg, 3.1 mmol) and the reaction mixture was heated at 100° C. for 12 h. The reaction mixture was cooled to 0° C., filtered through a fritted funnel, and concentrated in vacuo. To this crude reaction mixture was added 95% ethanol (300 mL) and silver nitrate (15.1 g, 88.8 mmol), and the reaction mixture was refluxed for 4 h, cooled to room temperature, filtered through a fritted funnel, and concentrated in vacuo. Purification by medium pressure liquid chromatography (SiO2, 10:1 hexanes/ethyl acetate) gave 880 mg (13%, 2 steps) of the title compound. MS 174 (M+H)+.

1. temperatureThe reaction mixture was cooled to 0° C.
2. filtrationfiltered through a fritted funnel
3. concentrationconcentrated in vacuo
4. customTo this crude reaction mixture
5. temperaturethe reaction mixture was refluxed for 4 h
6. temperaturecooled to room temperature
7. filtrationfiltered through a fritted funnel
8. concentrationconcentrated in vacuo
9. customPurification by medium pressure liquid chromatography (SiO2, 10:1 hexanes/ethyl acetate)