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

HRID 2204206ノート

反応式

HRID 2204206 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-0102ff226cb343a095c3b66dbfb758ba
出典データセット
uspto-grants-2016_06
特許番号
US09365588B2

反応ノート

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