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

HRID 394635노트

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HRID 394635 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매2회HCID 5943Carbon Tetrachloride용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-174b2d4714da47b4ba1fe96d04b8e68f
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06602901B2

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