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

HRID 1603030Notes

Reaction equation

HRID 1603030 reaction equation
[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].C1C(=O)N([Br:23])C(=O)C1>C1COCC1>[Br:23][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

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 145136N-Triisopropylsilylpyrrole

Product 1

HCID 27633023-Bromo-1-(triisopropylsilyl)pyrroleYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a -78° C. solution under nitrogen of 1-triisopropylsilylpyrrole (2.8 g, 12.6 mmol) in THF (30 ml) was added NBS (2.23 g, 12.6 mmol) via a solid addition funnel. The reaction mixture was stirred at -78° C. for 1 hour and then was warmed to ambient temperature over 1 hour. The reaction mixture was concentrated, carbon tetrachloride was added to precipitate the succinimide and the solid was filtered and washed with carbon tetrachloride. The filtrate was concentrated, and the crude product was purified by flash chromatography (hexanes) to afford 3-bromo-1-triisopropylsilylpyrrole (3.18 g) as a colorless oil.

Workup

  1. additionvia a solid addition funnel
  2. temperaturewas warmed to ambient temperature over 1 hour
  3. concentrationThe reaction mixture was concentrated
  4. additioncarbon tetrachloride was added
  5. customto precipitate the succinimide
  6. filtrationthe solid was filtered
  7. washwashed with carbon tetrachloride
  8. concentrationThe filtrate was concentrated
  9. customthe crude product was purified by flash chromatography (hexanes)

Sources & evidence

ORD record
ord-3fe1811665254a9fa9c8a9ab22115587
Source dataset
uspto-grants-1999_11
Patent number
US05985911

Reaction notes

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