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

HRID 1908123ノート

反応式

HRID 1908123 の反応式
[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

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 585508625-Isopropoxyquinoline

生成物 1

HCID 585509768-Bromo-5-isopropoxy-quinoline収率 92%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d2dfd788fe3846daaeb977ef0b2acde1
出典データセット
uspto-grants-2013_12
特許番号
US08598164B2

反応ノート

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