反応 #158838

反応方程式

EtOH

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

4-methylphenylboronic acid

potassium carbonate

toluene

→

title compound

収率 82.7%

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

収率 82.7%

溶媒

water

EtOAc

Water

反応条件

後処理

1. 1
   温度cooled to room temperature
2. 2
   洗浄The mixture was washed with saturated aqueous NaCl
3. 3
   抽出extracted with EtOAc
4. 4
   乾燥dried over MgSO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他to yield a red solid
8. 8
   その他The product was triturated with 1:1 EtOAc
9. 9
   ろ過hexanes, filtered
10. 10
    洗浄rinsed with hexanes
11. 11
    その他to yield a reddish-brown solid
12. 12
    その他The product was triturated with EtOAc
13. 13
    ろ過filtered
14. 14
    洗浄rinsing with EtOAc

実験手順

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.

出典