反应 #84032

反应方程式

6-bromo-N-methoxy-N-methyl-2-naphthamide

methyl magnesium bromide

hydrochloric acid

→

1-(6-bromonaphthalen-2-yl)-ethanone

收率 99.0%

溶剂

tetrahydrofurane

反应条件

后处理

1. 1
   温度The reaction mixture was cooled in an ice bath
2. 2
   温度carefully added drop wise while cooling on an ice bath
3. 3
   其他The organic solvent was evaporated
4. 4
   萃取the precipitated product extracted with dichloromethane (500 mL)
5. 5
   干燥The solution was dried over sodium sulphate
6. 6
   过滤filtered
7. 7
   浓缩concentrated
8. 8
   其他The solid residue was dried in vacuum at 40° C.

实验过程

6-bromo-N-methoxy-N-methyl-2-naphthamide (82.9 g, 282 mmol, 1 equiv.) was dissolved in tetrahydrofurane (600 mL) in a 4-neck flask under nitrogen. The reaction mixture was cooled in an ice bath and methyl magnesium bromide (3.2 M in methyl-tetrahydrofurane, 197 mL, 2.2 equiv.) was added drop wise during 1 hour, while maintaining the temperature of the reaction mixture between 10-15° C. The reaction mixture was stirred 30 minutes further in an ice bath. Aqueous hydrochloric acid (2 M, 100 mL) was then carefully added drop wise while cooling on an ice bath. The organic solvent was evaporated and the precipitated product extracted with dichloromethane (500 mL). The solution was dried over sodium sulphate, filtered and concentrated. The solid residue was dried in vacuum at 40° C. yielding 1-(6-bromonaphthalen-2-yl)-ethanone (70.6 g, 99%).

来源