Indoline → HCID 18629224, Verbindung

HRID 1271152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271152
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Br-:10].[Br-:11].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[Br:10][C:6]1[CH:5]=[C:4]2[C:9](=[C:8]([Br:11])[CH:7]=1)[NH:1][CH2:2][CH2:3]2

Komponenten

4

Edukt 2

HCID 10328IndolineHCID 21124087Pyridiniumtribromide

Produkt 1

HCID 18629224HCID 18629224, VerbindungAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Part A: Indoline (2.2 g, 18.04 mmol), dissolved in dichloromethane (160 mL) was stirred with pyridinium tribromide (12 g, 37.6 mmol) for 16 h at 25° C. The reaction was quenched with sat NaHSO3 (50 mL) and water (50 mL). The dichloromethane was separated, dried (MgSO4) and stripped in vacuo. The residue was chromatographed on silica gel using 20% ethyl acetate/hexanes as eluent to give 5,7-dibromoindoline (4.2 g, 84% yield). 1H NMR(CDCl3) δ 7.28 (m, 1H), 7.11 (s, 1H), 3.96 (s br, 1H ), 3.63 (t J=9 Hz, 1H), 3.13 (t J=9 Hz, 2H).

Aufarbeitung

  1. customThe reaction was quenched with sat NaHSO3 (50 mL) and water (50 mL)
  2. customThe dichloromethane was separated
  3. dry with materialdried (MgSO4)
  4. customThe residue was chromatographed on silica gel using 20% ethyl acetate/hexanes as eluent

Quellen und Nachweise

ORD-Eintrag
ord-76f19e53dee44d659a2d4af7c775bd0e
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205306B2

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