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

HRID 1780907Notes

Reaction equation

HRID 1780907 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].[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

Participants

4

Reactant 2

HCID 145136N-TriisopropylsilylpyrroleHCID 9834204N-Bromosuccinamide

Product 1

HCID 27633023-Bromo-1-(triisopropylsilyl)pyrroleYield 58.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3f54e9fca67143dcba827aa0a2909574
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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