تفاعل #158888

معادلة التفاعل

NBS

3,9-dibromo-5,7-dihydro-dibenzo[c,e]oxepine

tributyl(ethoxyvinyl)stannane

Water

→

2-bromo-1-(9-bromo-5,7-dihydro-dibenzo[c,e]oxepin-3-yl)-ethanone

المردود 25.2%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas cooled to 0° C
2. 2
   أخرىthe solvent was removed under reduced pressure
3. 3
   workup.ADDITIONThe mixture was diluted with EtOAc
4. 4
   غسيلwas washed with water and brine
5. 5
   تجفيفdried with sodium sulfate
6. 6
   تركيزConcentration and purification by flash column chromatography (hexane/EtOAc)

الإجراء التجريبي

To the solution of 3,9-dibromo-5,7-dihydro-dibenzo[c,e]oxepine (416 mg, 1.2 mmol) and tributyl(ethoxyvinyl)stannane (878 μl, 2.6 mmol) in dioxane (6 ml) was added PdCl2(PPh3)2 (30 mg). The mixture was heated at 80° C. for 16 hours and was cooled to 0° C. Water (2 ml) was added, followed by slow addition of NBS (464 mg, 2.6 mmol) over 5 minutes period. The mixture was stirred at 0° C. for additional 40 minutes, and the solvent was removed under reduced pressure. The mixture was diluted with EtOAc, and was washed with water and brine and dried with sodium sulfate. Concentration and purification by flash column chromatography (hexane/EtOAc) gave 2-bromo-1-(9-bromo-5,7-dihydro-dibenzo[c,e]oxepin-3-yl)-ethanone (120 mg).

المصدر