反应详情

温度

70 °C

2-Bromo-N-[1-dimethylaminometh-(E)-ylidene]-benzenesulfonamide (5.4 g, 18.4 mmol), 4-methylphenylboronic acid (5.0 g, 36.8 mmol) and potassium carbonate (5.1 g, 36.8 mmol) were dissolved in water (19.7 mL, 1090 mmol), EtOH (49.2 mL, 842 mmol) and toluene (98.3 mL, 923 mmol). The resulting mixture was stirred under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmol) was added. The mixture was heated at 60° C. for 115 minutes, at 70° C. for 30 minutes, then cooled to room temperature. Water (100 mL) and EtOAc (100 mL) were added. The mixture was washed with saturated aqueous NaCl, extracted with EtOAc, dried over MgSO4, filtered, and concentrated to yield a red solid. The product was triturated with 1:1 EtOAc:hexanes, filtered, and rinsed with hexanes to yield a reddish-brown solid. The product was triturated with EtOAc, filtered, and rinsing with EtOAc to yield the title compound (4.6 g) as a light brown solid.

1. temperaturecooled to room temperature
2. washThe mixture was washed with saturated aqueous NaCl
3. extractionextracted with EtOAc
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto yield a red solid
8. customThe product was triturated with 1:1 EtOAc
9. filtrationhexanes, filtered
10. washrinsed with hexanes
11. customto yield a reddish-brown solid
12. customThe product was triturated with EtOAc
13. filtrationfiltered
14. washrinsing with EtOAc