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

HRID 1908123노트

반응식

HRID 1908123 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-d2dfd788fe3846daaeb977ef0b2acde1
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598164B2

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