N-bromobutanimide → 12-bromo-2,10-dichloro-12H-5,7-dioxadibenzo[a,d]cyclooctene

HRID 394635ノート

反応式

HRID 394635 の反応式
[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

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 149005562,10-dichloro-12H-dibenzo[d,g][1,3]dioxocine

生成物 1

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

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒2 回HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-174b2d4714da47b4ba1fe96d04b8e68f
出典データセット
uspto-grants-2003_08
特許番号
US06602901B2

反応ノート

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