反应详情

温度

80 °C

1-(5-Bromo-2-hydroxyphenyl)-2-methylpropan-1-one (0.82 g, 3.37 mmol) was dissolved in EtOH (10 mL) then hydroxylamine (50% solution in water, 0.267 g, 4.05 mmol) was added followed by HOAc (1 drop). The mixture was heated to about 80° C. for about 2 h. The mixture was cooled then evaporated under reduced pressure to give an oil. Acetic anhydride (2 mL, 20 mmol) was added and the mixture was stirred for about 45 min at ambient temperature. The mixture was concentrated under reduced pressure then pyridine (7 mL) was added and then the mixture was heated to about 145° C. for about 3 h. The mixture was cooled, treated with 1 N HCl, and extracted with EtOAc. The organic extract was dried over MgSO4, filtered and evaporated to a residue that was then dissolved in DME (4 mL). Cesium carbonate (1.09 g, 3.35 mmol) was added and the mixture was heated at about 150° C. for about 30 min in the microwave. The mixture was evaporated and then purified by flash chromatography with 9:1 heptane/EtOAc to give the title compound (0.12 g, 15%): LC/MS (Table 1, Method a) Rt=3.33 min; MS m/z: 340.1 (M+H)+.

1. temperatureThe mixture was cooled
2. customthen evaporated under reduced pressure
3. customto give an oil
4. concentrationThe mixture was concentrated under reduced pressure
5. additionpyridine (7 mL) was added
6. temperaturethe mixture was heated to about 145° C. for about 3 h
7. temperatureThe mixture was cooled
8. additiontreated with 1 N HCl
9. extractionextracted with EtOAc
10. extractionThe organic extract
11. dry with materialwas dried over MgSO4
12. filtrationfiltered
13. customevaporated to a residue that
14. dissolutionwas then dissolved in DME (4 mL)
15. temperaturethe mixture was heated at about 150° C. for about 30 min in the microwave
16. customThe mixture was evaporated
17. custompurified by flash chromatography with 9:1 heptane/EtOAc