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

HRID 1451350

Reaction equation

HRID 1451350 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), 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 eluent 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 eluent was concentrated in vacuo
  6. distillationthe residue was distilled (b.p. 107°-108° C./0.2 mm)

Sources & evidence

ORD record
ord-4a471699db2c4eebb74bb36690c97b31
Source dataset
uspto-grants-1997_02
Patent number
US05604224

Linked notes

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