Benzoyl Peroxide → Methyl 2-(bromo-methyl)-4-chloro-1-methyl-1H-indole-3-carboxylate

HRID 453855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453855
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:13]([O:15][CH3:16])=[O:14])=[C:5]([CH3:12])[N:6]2[CH3:11].C1C(=O)N([Br:24])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:24][CH2:12][C:5]1[N:6]([CH3:11])[C:7]2[C:3]([C:4]=1[C:13]([O:15][CH3:16])=[O:14])=[C:2]([Cl:1])[CH:10]=[CH:9][CH:8]=2

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 59473668Methyl 4-chloro-1,2-dimethyl-1H-indole-3-carboxylate

Produkt 1

HCID 59473756Methyl 2-(bromo-methyl)-4-chloro-1-methyl-1H-indole-3-carboxylateAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Methyl 4-chloro-1,2-dimethyl-1H-indole-3-carboxylate (9.70 mmol, 1.0 equiv.) was dissolved in CCl4 (97 ml), and NBS (9.70 mmol, 1.0 equiv.) and benzoyl peroxide (0.19 mmol, 0.02 equiv.) were added. The mixture was heated for 1 h at 85° C. The resulting succinimide was filtered out, the filtrate was concentrated, and the residue was purified by column chromatography (20% ethyl acetate in hexane). Yield: 48%

Aufarbeitung

  1. filtrationThe resulting succinimide was filtered out
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by column chromatography (20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-41a85795b6ca4f81ae7b4d6bfb8f6e9c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492559B2

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