Reaktion #158838

Reaktionsgleichung

EtOH

2-Bromo-N-[1-dimethylaminometh-(E)-ylidene]-benzenesulfonamide

4-methylphenylboronic acid

potassium carbonate

toluene

→

title compound

Ausbeute 82.7%

4′-Methylbiphenyl-2-sulfonic acid 1-dimethylaminometh-(E)-ylideneamide

Ausbeute 82.7%

Lösungsmittel

water

EtOAc

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   WaschenThe mixture was washed with saturated aqueous NaCl
3. 3
   Extraktionextracted with EtOAc
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   Sonstigeto yield a red solid
8. 8
   SonstigeThe product was triturated with 1:1 EtOAc
9. 9
   Filtrationhexanes, filtered
10. 10
    Waschenrinsed with hexanes
11. 11
    Sonstigeto yield a reddish-brown solid
12. 12
    SonstigeThe product was triturated with EtOAc
13. 13
    Filtrationfiltered
14. 14
    Waschenrinsing with EtOAc

Vorschrift

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.

Quelle