N-bromobutanimide → HCID 86652237, compound

HRID 1849934Notes

Reaction equation

HRID 1849934 reaction equation
[CH:1]([SiH:4]([CH:11]([CH3:13])[CH3:12])[C:5]#[C:6][Si:7]([CH3:10])([CH3:9])[CH3:8])([CH3:3])[CH3:2].[Br:14]N1C(=O)CCC1=O>ClC(Cl)C>[CH:11]([Si:4]([Br:14])([CH:1]([CH3:3])[CH3:2])[C:5]#[C:6][Si:7]([CH3:9])([CH3:8])[CH3:10])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 101337817HCID 101337817, compound

Product 1

HCID 86652237HCID 86652237, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Diisopropyl(trimethylsilylethynyl)silane (6.9 g, 33 mmol) was dissolved in dichloroethane (20 mL) in a round-bottom flask equipped with a stir bar and placed in an ice bath. N-Bromosuccinimide (36 mmol, 6.5 g) was added scoopwise over 30 minutes, and stirring was continued for 15 more minutes or until the solution began to turn bright orange. Solvent was removed using rotary evaporation, pentane was added to the resulting solid, and the remaining solid succinimide residues were removed by filtration. The pentane solution was again evaporated, the process repeated, and the pentane was removed to yield 8.6 g (29 mmol, 89%) of a product as a pale brown oil.

Workup

  1. customequipped with a stir bar
  2. customplaced in an ice bath
  3. customSolvent was removed
  4. customevaporation, pentane
  5. additionwas added to the resulting solid
  6. customthe remaining solid succinimide residues were removed by filtration
  7. customThe pentane solution was again evaporated
  8. customthe pentane was removed

Sources & evidence

ORD record
ord-ad357201b6c54beeae4087bdef524bd4
Source dataset
uspto-grants-2015_02
Patent number
US08956555B2

Reaction notes

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