반응 #9369

반응 방정식

3-Ethoxy-cyclopent-2-enone

NBS

→

2-bromo-3-ethoxy-cyclopent-2-enone

용매

carbon tetrachloride

반응 조건

후처리

1. 1
   workup.ADDITIONadded portion-wise over 30 m
2. 2
   기타After 1 h at 0° C. the mixture was partitioned between CH2Cl2 and saturated NaHCO3
3. 3
   추출The aqueous layer was extracted with CH2Cl2
4. 4
   세척The pooled organic layers were washed with H2O (2×)
5. 5
   건조dried over MgSO4
6. 6
   여과The mixture was filtered
7. 7
   기타evaporated to dryness
8. 8
   기타The solid was recrystallized from pentane

실험 절차

3-Ethoxy-cyclopent-2-enone (Intermediate NINE1) (commercially available from Aldrich) (10.0 g, 77.6 mmol) in carbon tetrachloride (15 mL) at 0° C. was treated with NBS (15.3 g, ˜85 mmol) added portion-wise over 30 m. After 1 h at 0° C. the mixture was partitioned between CH2Cl2 and saturated NaHCO3. The aqueous layer was extracted with CH2Cl2. The pooled organic layers were washed with H2O (2×) and dried over MgSO4. The mixture was filtered and evaporated to dryness. The solid was recrystallized from pentane:ether to give 13.3 g of 2-bromo-3-ethoxy-cyclopent-2-enone (Intermediate NINE2).

출처