反应详情

温度

100 °C

4′-Methylbiphenyl-2-sulfonic acid 1-dimethylaminometh-(E)-ylideneamide (540.0 mg, 1786 μmol), NBS (318 mg, 1.8 mmol), and benzoyl peroxide (4.3 mg, 17.8 μmol) were dissolved in chlorobenzene (7.0 mL, 69 mmol) and the resulting solution was heated at 100° C. for 90 minutes. The mixture was cooled to room temperature and water was added. The mixture was extracted with DCM, washed with saturated NaHCO3 and saturated aqueous NaCl, extracted again with DCM, dried over MgSO4, filtered, and concentrated. The crude product was purified by flash chromatography (40 g, 0-100% EtOAc in hexanes), then taken up in EtOAc (4.5 mL) and DCM (1.5 mL). Additional DCM (3.0 mL) was added and the mixture was heated at 60° C. The mixture was cooled in the freezer overnight, then concentrated. The material was taken up in DCM (2 mL), EtOAc (6 mL) was added, and the resulting solution placed in the freezer. A precipitate formed and was filtered to yield the title compound (279 mg) as a white solid.

1. temperatureThe mixture was cooled to room temperature
2. extractionThe mixture was extracted with DCM
3. washwashed with saturated NaHCO3 and saturated aqueous NaCl
4. extractionextracted again with DCM
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product was purified by flash chromatography (40 g, 0-100% EtOAc in hexanes)
9. additionAdditional DCM (3.0 mL) was added
10. temperaturethe mixture was heated at 60° C
11. temperatureThe mixture was cooled in the freezer overnight
12. concentrationconcentrated
13. additionEtOAc (6 mL) was added
14. customA precipitate formed
15. filtrationwas filtered