반응 #46459

반응 방정식

1-Bromo-3-iodo-5-methyl-2-(3-phenylallyloxy)-benzene

sodium carbonate

sodium formate

→

3-benzyl-7-bromo-5-methyl-benzofuran

수율 52.7%

용매

DMF

반응 조건

후처리

1. 1
   기타The mixture was degassed
2. 2
   온도cooled to room temperature
3. 3
   workup.ADDITIONWater was added
4. 4
   추출the mixture was extracted with a hexanes/ethyl acetate (1:1) mixture
5. 5
   기타The solution was dried onto 20 gm silica gel
6. 6
   기타the silica gel was layered over 100 gm silica gel in a fritted funnel
7. 7
   세척eluted with four 400 ml portions of hexanes
8. 8
   기타The hexanes was removed under reduced pressure

실험 절차

1-Bromo-3-iodo-5-methyl-2-(3-phenylallyloxy)-benzene (10.86 g, 25 mmol), tetrabutylammonium chloride (7.65 gm, 27.5 mmol), sodium carbonate (6.62 g, 62.46 mmol), sodium formate (1.7 g, 25 mmol), and bis(acetonitrile)dichloropalladium(II) (0.467 g, 1.8 mmol) was added to 50 ml DMF. The mixture was degassed and heated under nitrogen at 80° C. for 105 minutes, then cooled to room temperature. Water was added and the mixture was extracted with a hexanes/ethyl acetate (1:1) mixture. The solution was dried onto 20 gm silica gel, the silica gel was layered over 100 gm silica gel in a fritted funnel and eluted with four 400 ml portions of hexanes. The hexanes was removed under reduced pressure to give 3-benzyl-7-bromo-5-methyl-benzofuran (3.97 g, 52% yield). MS: (M+H)+ 302.

출처