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

HRID 1908123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1908123
[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

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 585508625-Isopropoxyquinoline

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d2dfd788fe3846daaeb977ef0b2acde1
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598164B2

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