Реакция #46459

Уравнение реакции

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

sodium carbonate

sodium formate

→

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

Выход 52.7%

Растворители

DMF

Условия реакции

Обработка

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

Методика

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.

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