N-Triisopropylsilylpyrrole → 3-Bromo-1-(triisopropylsilyl)pyrrole

HRID 742482

Reaktionsgleichung

Reaktionsgleichung von HRID 742482
[CH:1]([Si:4]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[N:5]1[CH:9]=[CH:8][CH:7]=[CH:6]1)([CH3:3])[CH3:2].[Br:16]NC(=O)CCC(N)=O>C1COCC1>[Br:16][C:7]1[CH:8]=[CH:9][N:5]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:10]([CH3:12])[CH3:11])[CH:13]([CH3:15])[CH3:14])[CH:6]=1

Komponenten

4

Edukt 2

HCID 145136N-TriisopropylsilylpyrroleHCID 9834204N-Bromosuccinamide

Produkt 1

HCID 27633023-Bromo-1-(triisopropylsilyl)pyrroleAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 1-triisoproylsilyl-pyrrole (13.2 g, 0.059 mol) in 250 mL of THF at -78° C. was added 10.45 g (0.0587 mol) of N-bromosuccinamide (NBS), and the mixture was stirred at -78° C. for 3 h. The reaction mixture was warmed to room temperature and concentrated in vacuo, and the resulting residue in hexane was stirred overnight. The hexane solution was filtered through alumina eluting with hexane, the eluate was concentrated in vacuo, and the residue was distilled (b.p. 107°-108° C./0.2 mm) to afford 10.4 g (58.4%) of 3-bromo-1-triisopropylsilyl-pyrrole.

Aufarbeitung

  1. temperatureThe reaction mixture was warmed to room temperature
  2. concentrationconcentrated in vacuo
  3. stirringthe resulting residue in hexane was stirred overnight
  4. filtrationThe hexane solution was filtered through alumina eluting with hexane
  5. concentrationthe eluate was concentrated in vacuo
  6. distillationthe residue was distilled (b.p. 107°-108° C./0.2 mm)

Quellen und Nachweise

ORD-Eintrag
ord-2a6d6d4f48334de1a8929e625669078a
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05554620

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