Azobisisobutyronitrile → 8-Bromo-2-(bromomethyl)quinoline

HRID 499979

Reaktionsgleichung

Reaktionsgleichung von HRID 499979
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.C1C(=O)N([Br:20])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH2:12][Br:20])[CH:8]=[CH:7]2

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 47150308-Bromo-2-methylquinoline

Produkt 1

HCID 574568018-Bromo-2-(bromomethyl)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a solution of 2 (2.5477 g, 11.47 mmol) in carbon tetrachloride (40 mL) was added NBS (2.2461 g, 12.62 mmol) and a little bit of AIBN followed by refluxing overnight under UV light. The mixture was filtered to remove the solid and concentrated to give a yellow solid. Purification by chromatography (hexanes/DCM 80:20) yielded a white solid.(1.33 g, 39%) 1H NMR (400 MHz CDCl3) δ8.16 (1H, d, J=8.4 Hz), 8.05 (1H, d, J=7.2 Hz), 7.78 (1H, d, J=7.6 Hz), 7.65 (1H, d, J=8.4 Hz), 7.41 (1H, t, J=7.6 Hz), 4.78 (3H, s); 13C NMR (300 MHz CDCl3) δ158.3, 144.7, 138.0, 133.9, 128.9, 127.7, 127.6, 125.1, 122.4, 34.6; EIMS, m/z 299/300/301 (M/M+1/M+2).

Aufarbeitung

  1. temperatureby refluxing overnight under UV light
  2. filtrationThe mixture was filtered
  3. customto remove the solid
  4. concentrationconcentrated
  5. customto give a yellow solid
  6. customPurification by chromatography (hexanes/DCM 80:20)
  7. customyielded a white solid

Quellen und Nachweise

ORD-Eintrag
ord-323fa65a3a2a402380e6bfa6cfdfe19c
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767817B2

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