反应详情

温度

80 °C

The mixture of tert-butyl 3-bromobenzoate (7.0 g, 27.2 mmol), sodium methanesulfinate (4.45 g, 43.6 mmol), copper(I) iodide (0.52 g, 2.72 mmol), L-proline (0.63 g, 5.44 mmol) and sodium hydroxide (0.22 g, 5.44 mmol) was purged with nitrogen and DMSO was added. The mixture was heated to 80° C. After 18 h, the mixture was cooled to ambient temperature. Additional sodium methanesulfinate (2.78 g, 27.2 mmol), copper(I) iodide (0.52 g, 2.72 mmol), L-proline (0.63 g, 5.44 mmol) were added and the mixture was stirred at 80° C. for another 18 h. The mixture was cooled to ambient temperature and filtered with Celite. Lithium chloride (3.0 M in water) was added and the mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with LiCl (3.0 M in water), brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→75% hexanes/ethyl acetate) gave the title compound (5.05 g).

1. customwas purged with nitrogen and DMSO
2. additionwas added
3. temperaturethe mixture was cooled to ambient temperature
4. temperatureThe mixture was cooled to ambient temperature
5. filtrationfiltered with Celite
6. additionLithium chloride (3.0 M in water) was added
7. extractionthe mixture was extracted with ethyl acetate (3×)
8. washThe combined organic extracts were washed with LiCl (3.0 M in water), brine
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. customPurification by silica gel chromatography (100% hexanes→75% hexanes/ethyl acetate)