N-bromobutanimide → HCID 58179610, compound

HRID 254004Notes

Reaction equation

HRID 254004 reaction equation
[C:1]([Si:5]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[N:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2].[Br:17]N1C(=O)CCC1=O>C1COCC1.C(Cl)(Cl)(Cl)Cl>[C:1]([Si:5]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:12])[CH3:13])[N:6]1[CH:7]=[CH:8][C:9]([Br:17])=[CH:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 58180031HCID 58180031, compound

Product 1

HCID 58179610HCID 58179610, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(tert-butyldiisopropylsilyl)-1H-pyrrole (1.0 g, 4.48 mmol) in THF was added N-bromosuccinimide at −78° C. The reaction mixture was slowly warmed to RT and stirred for 24 hours. The reaction mixture was concentrated to obtain dark black residue, which was suspended in CCl4 (100 mL) and stirred for 15 min and filtered. The filtrate was concentrated to obtain 1-(tert-butyldiisopropylsilyl)-3-bromo-1H-pyrrole as oily liquid (1.0 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto obtain dark black residue, which
  3. stirringstirred for 15 min
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-36ef13acad39448ba4e4090841966be4
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

Loading…