N-bromobutanimide → 8-Bromo-5-isopropoxy-quinoline

HRID 2204206노트

반응식

HRID 2204206 반응식
[CH:1]([O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)([CH3:3])[CH3:2].C1C(=O)N([Br:22])C(=O)C1>C(#N)C>[Br:22][C:12]1[CH:13]=[CH:14][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 585508625-Isopropoxyquinoline

생성물 1

HCID 585509768-Bromo-5-isopropoxy-quinoline수율 92%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 5-isopropoxyquinoline (1.87 g, 10.0 mmol) in acetonitrile (100 mL) was added NBS (1.78 g, 10.0 mmol) at 0° C. The mixture was stirred at rt for 2 h before the solvent was removed. The residue was partitioned between EtOAc and H2O. The layers were separated and the organic layer was washed with brine, dried over MgSO4, and concentrated. The crude material was purified by column chromatography (0-10% EtOAc-Hex) to provide 8-bromo-5-isopropoxy-quinoline (92%) as a light brown solid. ESI-MS m/z calc 265.1, found 266.1 (M+1)+. Retention time: 1.44 minutes (3 min run).

후처리

  1. customwas removed
  2. customThe residue was partitioned between EtOAc and H2O
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography (0-10% EtOAc-Hex)

출처 및 근거

ORD 기록
ord-0102ff226cb343a095c3b66dbfb758ba
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365588B2

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