反应详情

温度

80 °C

A screw cap vial was charged with 4-bromo-2-nitroaniline (7.00 g, 32.3 mmol), xantphos (0.933 g, 1.613 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.738 g, 0.806 mmol), 1,4-Dioxane (32.3 ml), and DIPEA (11.22 ml, 64.5 mmol). The vial was purged with Argon, sealed and heated to 80° C. for 10 minutes. The reaction was cooled to room temperature and benzyl mercaptan (4.01 ml, 33.9 mmol) was added and the reaction heated at 80° C. for 3 hours. The reaction was cooled to room temperature, diluted with water and extracted with DCM (3×). The combined organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The resulting material was concentrated, dissolved in minimal DCM and purified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane) to afford 4-(benzylthio)-2-nitroaniline (7.43 g, 28.5 mmol, 88% yield). m/z (ESI) 261.2 (M+H)+.

1. customA screw cap vial
2. customThe vial was purged with Argon
3. customsealed
4. temperatureThe reaction was cooled to room temperature
5. temperaturethe reaction heated at 80° C. for 3 hours
6. temperatureThe reaction was cooled to room temperature
7. extractionextracted with DCM (3×)
8. washThe combined organics were washed with water and brine
9. dry with materialdried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. concentrationThe resulting material was concentrated
13. dissolutiondissolved in minimal DCM
14. custompurified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane)