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

HRID 356602

Reaction equation

HRID 356602 reaction equation
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

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 145136N-Triisopropylsilylpyrrole

Product 1

HCID 27633023-Bromo-1-(triisopropylsilyl)pyrroleYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2069c0804a554713866128ef5b2f12e5
Source dataset
uspto-grants-1998_11
Patent number
US05837704

Linked notes

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