反应详情

An oven-dried flask was charged with BBr3.SMe2 (2.80 g, 9.20 mmol) and 1,2-dichloroethane (15 mL). 5-Methoxyindolin-2-one (0.30 g, 1.84 mmol) was then added and the mixture was heated to reflux for 18 hours. The reaction was then cooled to room temperature and quenched with MeOH (1.0 mL). The mixture was then extracted into EtOAc washing with brine (3×). The organic layer was dried over MgSO4, filtered and the solvent removed in vacuo; the resulting residue was then purified by column chromatography (silica gel, 94:6 to 92:8, CH2Cl2/MeOH) to give 144 mg, 53% of a beige powder. MS ESI 149.9 [M+H]+, calcd for [C8H7NO2+H]+ 150.06

1. temperaturethe mixture was heated
2. temperatureto reflux for 18 hours
3. customquenched with MeOH (1.0 mL)
4. extractionThe mixture was then extracted into EtOAc washing with brine (3×)
5. dry with materialThe organic layer was dried over MgSO4
6. filtrationfiltered
7. customthe solvent removed in vacuo
8. customthe resulting residue was then purified by column chromatography (silica gel, 94:6 to 92:8, CH2Cl2/MeOH)