تفاعل #46459

معادلة التفاعل

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

sodium carbonate

sodium formate

→

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

المردود 52.7%

المذيبات

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر