N-溴代丁二酰亚胺(NBS) → 12-bromo-2,10-dichloro-12H-5,7-dioxadibenzo[a,d]cyclooctene

HRID 394635笔记

反应方程式

HRID 394635 反应方程式
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[O:6][CH2:7][O:8][C:9]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:10]=3[CH2:11][C:4]=2[CH:3]=1.[Br:19]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:19][CH:11]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:18]=[CH:17][C:5]=2[O:6][CH2:7][O:8][C:9]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:10]1=2

参与物

5

反应物 2

HCID 67184N-溴代丁二酰亚胺(NBS)HCID 149005562,10-dichloro-12H-dibenzo[d,g][1,3]dioxocine

产物 1

HCID 2272777812-bromo-2,10-dichloro-12H-5,7-dioxadibenzo[a,d]cyclooctene收率 27%

试剂、催化剂与溶剂 2

HCID 6547偶氮二异丁腈催化剂2 次HCID 5943四氯化碳溶剂

反应条件

温度
80 °C

实验过程

To a solution of 2,10-dichloro-12H-dibenzo[d,g][1,3]-dioxocin (21.4 g, 76.1 mmol) and N-bromosuccinimide (13.5 g, 76.1 mmol) in tetrachloromethane (275 mL) was added azobisisobutyronitrile (200 mg, 1.2 mmol). The mixture was heated at 80° C. for 24 h. Another 3×azobisisobutyronitrile (200 mg, 1.2 mmol) was added within the 24 h. The mixture was filtrated and the solution phase concentrated in vacuo. The residue was added dichloromethane (30 mL) and ether (100 mL). The mixture was filtered and the solution phase concentrated in vacuo. The residue was submitted to flash chromatography eluting with heptane/ethyl acetate (3:1) to give 7.4 g (27%) of 12-bromo-2,10-dichloro-12H-5,7-dioxa-dibenzo[a,d]cyclooctene.

后处理

  1. filtrationThe mixture was filtrated
  2. concentrationthe solution phase concentrated in vacuo
  3. additionThe residue was added dichloromethane (30 mL) and ether (100 mL)
  4. filtrationThe mixture was filtered
  5. concentrationthe solution phase concentrated in vacuo
  6. washeluting with heptane/ethyl acetate (3:1)

来源与证据

ORD记录
ord-174b2d4714da47b4ba1fe96d04b8e68f
来源数据集
uspto-grants-2003_08
专利号
US06602901B2

反应笔记

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