反应详情

温度

95 °C

Methyl 4-bromo-2-fluoro-6-hydroxybenzoate (1.7 g, 5.6 mmol), sodium methanesulfinate (95%) (0.91 g, 8.5 mmol), CuI (0.64 g, 3.4 mmol), L-proline (0.78 g, 6.8 mmol) and K2CO3 (0.47 g, 3.4 mmol) was dissolved in DMSO (dry) (10 ml). Nitrogen was bubbled through the solution for 15 min. The mixture was stirred and heated at 95° C. for 6 h under nitrogen. After cooling to RT, the mixture was filtered on a plug of silica and eluted with ETOAc. The filtrate was washed with 1M citric acid. The waterlayer was extracted once with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated. Purification on flash column chromatography (isooctane/EtOAc) gave the crude title compound (0.14 g). MS m/z (rel. intensity, 70 eV) 248 (M+, 36), 216 (bp), 173 (19), 125 (20), 81 (24).

1. customNitrogen was bubbled through the solution for 15 min
2. temperatureAfter cooling to RT
3. filtrationthe mixture was filtered on a plug of silica
4. washeluted with ETOAc
5. washThe filtrate was washed with 1M citric acid
6. extractionThe waterlayer was extracted once with EtOAc
7. washThe combined organic phases were washed with brine
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customPurification on flash column chromatography (isooctane/EtOAc)