1-Bromo-2-nitrobenzene → 7-Bromo-2-methylindole

HRID 890237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 890237
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[C:11]([Mg]Br)([CH3:13])=[CH2:12].[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:8][C:11]([CH3:13])=[CH:12]2

Komponenten

5

Edukt 3

HCID 113411-Bromo-2-nitrobenzeneHCID 25517Ammonium ChlorideHCID 178456138HCID 178456138, Verbindung

Produkt 1

HCID 44130817-Bromo-2-methylindole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-55 °C

Versuchsvorschrift

27.0 g of 2-bromonitrobenzene are placed in 400 ml of THF. The medium is placed under nitrogen and is cooled to −55° C. and then 800 ml of 0.5M isopropenylmagnesium bromide in THF are added dropwise. The medium is left stirring for 1 hour and then it is poured into a saturated NH4Cl solution. Extraction is carried out with ether, the extract is evaporated and then the residue is taken up in DCM. Washing is carried out with a saturated NaCl solution. The organic layer is dried and evaporated and then the residue is chromatographed on silica while eluting with an AcOEt/cyclohexane (1/9, v/v) mixture. 10.7 g of the expected compound are obtained.

Aufarbeitung

  1. waitThe medium is left
  2. extractionExtraction
  3. customthe extract is evaporated
  4. washWashing
  5. customThe organic layer is dried
  6. customevaporated
  7. customthe residue is chromatographed on silica
  8. washwhile eluting with an AcOEt/cyclohexane (1/9, v/v) mixture

Quellen und Nachweise

ORD-Eintrag
ord-46f31e3bf53946d9b4fc969d470627b5
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995184B2

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