N-bromobutanimide → 3,6-Dibromo-1-(3-methoxypropyl)-1H-indole

HRID 656237

Reaktionsgleichung

Reaktionsgleichung von HRID 656237
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>O1CCCC1>[Br:16][C:6]1[C:5]2[C:9](=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=2)[N:8]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:7]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 231516746-Bromo-1-(3-methoxypropyl)-1H-indole

Produkt 1

HCID 686528323,6-Dibromo-1-(3-methoxypropyl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of 10.39 g of 6-bromo-1-(3-methoxypropyl)-1H-indole (building block 5) in 1.5 l of tetrahydrofuran is cooled to −78° C., and 7.05 g of N-bromosuccinimide are added. The mixture is stirred at −78° C. for 1.7 hours and then warmed to room temperature. The reaction mixture is evaporated. The title compound is obtained as an orange oil from the residue by flash chromatography (SiO2 60 F). Rf=0.31 (EtOAc-heptane 1:4); Rt=5.65 (Gradient I).

Aufarbeitung

  1. temperaturewarmed to room temperature
  2. customThe reaction mixture is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c69ef97162fb406ab0133ecdbc96b27e
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071651B2

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