Ammonium Chloride → 7-bromo-4-fluoro-1H-indole

HRID 387310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387310
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-])=O.[CH:12]([Mg]Br)=[CH2:13].[NH4+].[Cl-]>C1COCC1.COCCOC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]2[C:3]=1[NH:9][CH:13]=[CH:12]2

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 27733831-Bromo-4-fluoro-2-nitrobenzeneHCID 178418507HCID 178418507, Verbindung

Produkt 1

HCID 43429567-bromo-4-fluoro-1H-indoleAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of 1-bromo-4-fluoro-2-nitrobenzene (3.6 g, 16.4 mmol) in THF (100 mL) was added to a solution of 1 M vinylmagnesium bromide in THF (100 mL, 100 mmol) and DME (100 mL) at −78° C. (bath temp). The reaction was stirred at −78° C. for 4 h, and saturated aqueous NH4Cl was added. The layers were separated, and the organic layer was evaporated. The crude product was purified flash chromatography, giving 2 g (57%) of the title compound.

Aufarbeitung

  1. customThe layers were separated
  2. customthe organic layer was evaporated
  3. customThe crude product was purified flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d7fd7085fa87458d9192a55c5ca7e777
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372875B2

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