반응 #804272

반응 방정식

N,N-diisopropylamine

n-BuLi

4-bromobenzonitrile

N,N-diethyl-2,3-dimethyl-benzamide

→

3-(4-bromo-phenyl)-5-methyl-2H-isoquinolin-1-one

수율 58.4%

용매

—

n-hexanes

THF

THF

THF

반응 조건

후처리

1. 1
   온도the reaction mixture maintained at this temperature for 30 minutes
2. 2
   기타to give a deep red solution
3. 3
   기타The reaction mixture was quenched
4. 4
   workup.ADDITIONby adding dropwise onto ice, upon which a pale yellow solid
5. 5
   기타precipitated out
6. 6
   기타The solid was triturated with iso-hexane/EtOAc (2:1)
7. 7
   여과filtered
8. 8
   기타dried in vacuo

실험 절차

To N,N-diisopropylamine (2.54 mL, 18 mmol) in anhydrous THF (15 mL), under N2 at −78° C. was added n-BuLi dropwise (2.5M in n-hexanes, 7.2 mL, 18 mmol) and the reaction mixture maintained at this temperature for 30 minutes. A solution of N,N-diethyl-2,3-dimethyl-benzamide (1.23 g, 6 mmol) in anhydrous THF (15 mL) was added dropwise to give a deep red solution. After 20 minutes at −78° C., 4-bromobenzonitrile (1.09 g, 6 mmol) in anhydrous THF (15 mL) was added dropwise and the reaction mixture allowed to stir at this temperature for 2.5 h. The reaction mixture was quenched by adding dropwise onto ice, upon which a pale yellow solid precipitated out. The solid was triturated with iso-hexane/EtOAc (2:1), filtered and dried in vacuo to afford 3-(4-bromo-phenyl)-5-methyl-2H-isoquinolin-1-one as a pale yellow solid (1.1 g, 58%).

출처