StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

1-Bromo-2-iodobenzene → 2-(2-Bromophenyl)-1-(N,N-dimethylaminomethyl)ferrocene

HRID 1836744
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1836744
C([Li])(CC)C.[CH3:6][N:7]([CH2:9][C-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)[CH3:8].[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[Fe+2:20].[Br:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1I>C1CCCCC1.C1COCC1.C(OCC)C.[Cl-].[Cl-].[Zn+2]>[Br:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:11]1[C-:10]([CH2:9][N:7]([CH3:8])[CH3:6])[CH:14]=[CH:13][CH:12]=1.[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[Fe+2:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 114151-Bromo-2-iodobenzeneHCID 15764045cyclopenta-1,3-diene;1-cyclopenta-2,4-dien-1-yl-N,N-dimethylmethanamine;iron(2+)HCID 178418400CID 53628100

Produkt 1

HCID 1317245572-(2-Bromophenyl)-1-(N,N-dimethylaminomethyl)ferrocene

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 3007855ZincchlorideKatalysator
HCID 3283
Diethyl Ether
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×
HCID 8078CyclohexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

46 ml (60 mmol) of a 1.3 molar solution of s-butyllithium in cyclohexane are added dropwise to a degassed solution of 12 g (49.4 mmol) of N,N-dimethylaminomethylferrocene in 40 ml of THF while cooling in ice. The solution is stirred at 0° C. for 30 minutes, and 74 ml of a 1 molar solution of ZnCl2 in diethyl ether are subsequently added dropwise, likewise at 0° C. The reaction mixture is stirred at room temperature for 1 hour, after which 3.5 g (5 mmol) of bis(diphenylphosphine)palladium(II) chloride and a solution of 28.3 g (100 mmol) of 2-bromoiodobenzene in 50 ml of THF are added and the mixture is refluxed for 3 days. The solvent is taken off on a rotary evaporator, the residue is taken up in CH2Cl2 and extracted with water. The aqueous phase is extracted 3 times with 50 ml each time of CH2Cl2 and the combined organic phases are washed twice with 30 ml each time of water. After drying over MgSO4 and removal of the solvent under reduced pressure, the residue is chromatographed on aluminium oxide. As eluant, use is made of a mixture of petroleum ether, ether and triethylamine in a ratio of 60:1:3. The yield is 6.336 g (15.92 mmol, 32%) of L7.

Aufarbeitung

  1. temperaturewhile cooling in ice
  2. stirringThe reaction mixture is stirred at room temperature for 1 hour
  3. temperaturethe mixture is refluxed for 3 days
  4. customThe solvent is taken off on a rotary evaporator
  5. extractionextracted with water
  6. extractionThe aqueous phase is extracted 3 times with 50 ml each time of CH2Cl2
  7. washthe combined organic phases are washed twice with 30 ml each time of water
  8. dry with materialAfter drying over MgSO4 and removal of the solvent under reduced pressure
  9. customthe residue is chromatographed on aluminium oxide
  10. additionAs eluant, use is made of a mixture of petroleum ether, ether and triethylamine in a ratio of 60:1:3

Quellen und Nachweise

ORD-Eintrag
ord-cf24a3652e0b4114893a59ea0451ce64
Quelldatensatz
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06777567B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion