反応 #84032

反応方程式

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

methyl magnesium bromide

hydrochloric acid

→

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

収率 99.0%

溶媒

tetrahydrofurane

反応条件

後処理

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
   その他The organic solvent was evaporated
4. 4
   抽出the precipitated product extracted with dichloromethane (500 mL)
5. 5
   乾燥The solution was dried over sodium sulphate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他The solid residue was dried in vacuum at 40° C.

実験手順

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%).

出典