반응 #84032

반응 방정식

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

methyl magnesium bromide

hydrochloric acid

→

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

수율 99.0%

용매

tetrahydrofurane

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled in an ice bath
2. 2
   온도carefully added drop wise while cooling on an ice bath
3. 3
   기타The organic solvent was evaporated
4. 4
   추출the precipitated product extracted with dichloromethane (500 mL)
5. 5
   건조The solution was dried over sodium sulphate
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타The solid residue was dried in vacuum at 40° C.

실험 절차

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%).

출처