4-Chlorobutyronitrile → 4-(7-bromo-1H-indol-3-yl)butanenitrile

HRID 12623

Reaktionsgleichung

Reaktionsgleichung von HRID 12623
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.Cl[CH2:12][CH2:13][CH2:14][C:15]#[N:16].C([Mg]Br)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:12][CH2:13][CH2:14][C:15]#[N:16]

Komponenten

6

Edukt 4

HCID 123364-ChlorobutyronitrileHCID 25517Ammonium ChlorideHCID 27570207-BromoindoleHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 686933874-(7-bromo-1H-indol-3-yl)butanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To an anhydrous toluene (12 mL) solution of 7-bromoindole (1.0 g) and 4-chlorobutyronitrile (0.26 g), ethylmagnesium bromide (3.0M diethyl ether solution; 1.7 mL) was added dropwise under ice cooling and the mixture was heated to reflux for 4.5 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added under ice cooling, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and saturated saline, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10→70:30) to obtain the titled compound having the following physical properties (0.40 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4.5 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed in turn with water and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10→70:30)

Quellen und Nachweise

ORD-Eintrag
ord-27fdefc4bc05481e8d695825b2e4ecdb
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728023B2

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