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

HRID 1185634노트

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HRID 1185634 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[CH:12]=[CH:13][C:14]([Br:16])=[CH:15][C:10]=3[CH2:9][O:8][CH2:7][C:6]=2[CH:17]=1.C([Sn](CCCC)(CCCC)[CH:23]=[CH:24][O:25]CC)CCC.O.C1C(=O)N([Br:44])C(=O)C1>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:44][CH2:23][C:24]([C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[CH:12]=[CH:13][C:14]([Br:16])=[CH:15][C:10]=3[CH2:9][O:8][CH2:7][C:6]=2[CH:17]=1)=[O:25]

참가 물질

7

반응물 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)etheneHCID 223161653,9-Dibromo-5,7-dihydrodibenzo[c,e]oxepine

생성물 1

HCID 596102962-Bromo-1-(9-bromo-5,7-dihydro-dibenzo[c,e]oxepin-3-yl)-ethanone수율 25.2%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

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).

후처리

  1. temperaturewas cooled to 0° C
  2. customthe solvent was removed under reduced pressure
  3. additionThe mixture was diluted with EtOAc
  4. washwas washed with water and brine
  5. dry with materialdried with sodium sulfate
  6. concentrationConcentration and purification by flash column chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-8ecea14437f448deac2d26ec3b276926
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669234B2

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