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

HRID 722399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722399
[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 mixture is placed under nitrogen and cooled to −55° C. and then 800 ml of isopropenylmagnesium bromide at 0.5 M in THF are added dropwise. The mixture is left with stirring for 1 hour and then poured into saturated NH4Cl solution. It is extracted with ether, the extract is evaporated and then the residue is taken up in DCM. It is washed with saturated NaCl solution. It is dried and evaporated and then the residue is chromatographed on silica, eluting with an AcOEt/cyclohexane (1/9; v/v) mixture. This gives 10.7 g of the expected compound.

Aufarbeitung

  1. waitThe mixture is left
  2. extractionIt is extracted with ether
  3. customthe extract is evaporated
  4. washIt is washed with saturated NaCl solution
  5. customIt is dried
  6. customevaporated
  7. customthe residue is chromatographed on silica
  8. washeluting with an AcOEt/cyclohexane (1/9; v/v) mixture

Quellen und Nachweise

ORD-Eintrag
ord-8995fdecd0bb4973b3c445375ef1fde8
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138424B2

Notizen zur Reaktion

Wird geladen…