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

HRID 71705

반응식

HRID 71705 반응식
[Br:1][C:2]1C=C[C:5]2[C:11]3[CH:12]=[CH:13][C:14](Br)=[CH:15][C:10]=3[CH2:9]O[CH2:7][C:6]=2[CH:17]=1.C([Sn](CCCC)(CCCC)[CH:23]=[CH:24][O:25][CH2:26][CH3:27])CCC.[OH2:36].C1C(=O)N([Br:44])C(=O)C1.[O:45]1[CH2:50][CH2:49]OCC1>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:1][CH2:2][C:17]([C:6]1[CH:5]=[CH:11][C:12]2[C:13]3[CH:14]=[CH:15][C:10]([C:50](=[O:45])[CH2:49][Br:44])=[CH:9][C:23]=3[CH2:24][O:25][CH2:26][C:27]=2[CH:7]=1)=[O:36]

참가 물질

7

반응물 5

HCID 962WaterHCID 312751,4-DioxaneHCID 67184N-bromobutanimideHCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)etheneHCID 223161653,9-Dibromo-5,7-dihydrodibenzo[c,e]oxepine

생성물 1

HCID 596101462-Bromo-1-[9-(2-bromo-acetyl)-5,7-dihydro-dibenzo[c,e]oxepin-3-yl]-ethanone

시약·촉매·용매 1

HCID 178418476HCID 178418476, 화합물촉매

반응 조건

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-(2-bromo-acetyl)-5,7-dihydro-dibenzo[c,e]oxepin-3-yl]-ethanone (160 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-a27c72c2ed2a44b5af2aeef12d6ead7e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822430B2

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