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

HRID 356602

Reaktionsgleichung

Reaktionsgleichung von HRID 356602
C1C(=O)N([Br:8])C(=O)C1.[CH:9]([Si:12]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[N:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1)([CH3:11])[CH3:10]>C1COCC1>[Br:8][C:15]1[CH:16]=[CH:17][N:13]([Si:12]([CH:9]([CH3:11])[CH3:10])([CH:18]([CH3:20])[CH3:19])[CH:21]([CH3:23])[CH3:22])[CH:14]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 145136N-Triisopropylsilylpyrrole

Produkt 1

HCID 27633023-Bromo-1-(triisopropylsilyl)pyrroleAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

NBS (6.4 g) was added in one portion to a stirred solution of 1-(triisopropylsilyl)pyrrole (8.00 g) in dry THF (80 mL) at -78° C. The mixture was stirred at this temperature for 2 h, and was then allowed to warm to room temperature overnight. The solvent was removed, water was added to the residue, and the product extracted with CH2Cl2, dried (anhyd Na2SO4), filtered, and evaporated. The residue was chromatographed over silica gel (hexanes) and concentrated to provide 10.00 g of 3-bromo-1-(triisopropylsilyl)pyrrole as a colorless oil.

Aufarbeitung

  1. customThe solvent was removed
  2. additionwater was added to the residue
  3. extractionthe product extracted with CH2Cl2
  4. dry with materialdried (anhyd Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed over silica gel (hexanes)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2069c0804a554713866128ef5b2f12e5
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05837704

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