Chlorosuccinimide → 1-(5-Bromo-7-chloro-2,3-dihydro-1H-indol-1-yl)ethan-1-one

HRID 1060621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060621
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl:14]N1C(=O)CCC1=O>CC#N>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:13])=[CH:10][C:11]=2[Cl:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 31398Chlorosuccinimide2×HCID 7218471-(5-bromo-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Produkt 1

HCID 186292691-(5-Bromo-7-chloro-2,3-dihydro-1H-indol-1-yl)ethan-1-oneAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Part A: 1-Acetyl-5-bromoindoline (2.47 g, 10.29 mmol) was heated at reflux with N-chlorosuccinimide (1.56 g, 10.40 mmol) in CH3CN for 30 min and an additional amount NCS (1 g, 7.47 mmol) was added while hot and the reaction was stirred at 25° C. for 16 h. The solvent was stripped in vacuo and the residue was chromatographed on silica gel using 20% EtOAc/hexanes as eluent to give 1-acetyl-5-bromo-7-chloroindoline (1.17 g).

Aufarbeitung

  1. customthe residue was chromatographed on silica gel using 20% EtOAc/hexanes as eluent

Quellen und Nachweise

ORD-Eintrag
ord-a70b4a933b004f6fa8f962a69fd8646b
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525056B2

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