反応 #1583899

反応方程式

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

toluene

potassium carbonate

EtOH

4-methylphenylboronic acid

→

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

溶媒

EtOAc

water

water

反応条件

後処理

1. 1
   温度heated at 70° C. for 30 minutes
2. 2
   温度The mixture was then cooled to room temperature
3. 3
   洗浄The mixture was washed with saturated aqueous NaCl
4. 4
   抽出extracted with EtOAc
5. 5
   乾燥dried over MgSO4
6. 6
   ろ過filtered through Celite®
7. 7
   濃縮concentrated
8. 8
   その他to yield the crude product as a red solid (8.6 g)
9. 9
   その他The solid material was triturated with 1:1 EtOAc
10. 10
    ろ過hexanes, filtered
11. 11
    洗浄rinsed with hexanes
12. 12
    その他to yield the crude product as a reddish-brown solid (6.2 g)
13. 13
    その他The solid material was again triturated with EtOAc
14. 14
    ろ過filtered
15. 15
    洗浄rinsed with EtOAc

実験手順

2-Bromo-N-[1-dimethylaminometh-(E)-ylidene]benzenesulfonamide (5.36 g, 18.4 mmol), 4-methylphenylboronic acid (5.0 g, 36.8 mmol), potassium carbonate (5.1 g, 36.8 mmol), water (19.7 mL, 1090 mmol), EtOH (49.2 mL, 842 mmol) and toluene (98.3 mL, 923 mmol) were combined and the mixture was stirred under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmol) was then added. The mixture was heated at 60° C. for about 2 hours, then heated at 70° C. for 30 minutes. The mixture was then cooled to room temperature and water (100 mL) and EtOAc (100 mL) were added. The mixture was washed with saturated aqueous NaCl, extracted with EtOAc, dried over MgSO4, filtered through Celite® and concentrated to yield the crude product as a red solid (8.6 g). The solid material was triturated with 1:1 EtOAc:hexanes, filtered, and rinsed with hexanes to yield the crude product as a reddish-brown solid (6.2 g). The solid material was again triturated with EtOAc, filtered, and rinsed with EtOAc to yield 4′-methybiphenyl-2-sulfonic acid 1-dimethylaminometh-(E)-ylideneamide as a light brown solid (4.6 g; 96.2% purity).

出典