N-bromobutanimide → HCID 56949709, compound

HRID 1625177Notes

Reaction equation

HRID 1625177 reaction equation
[C:1]([SiH:4]([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])=[CH2:2].[Br:11]N1C(=O)CCC1=O>ClCCl>[C:1]([SiH:4]([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])=[CH2:2].[C:1]([Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[Br:11])([CH3:3])=[CH2:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 123518261HCID 123518261, compound

Product 2

HCID 56949709HCID 56949709, compoundHCID 123518261HCID 123518261, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude isopropenyldiisopropylsilane (10 g), which was prepared as described in “Preparation of Isopropenyldiisopropylsilane—Method 2” was taken up in dichloromethane (120 mL) and cooled in an ice bath. N-Bromosuccinimide (13.7 g, 77 mmol, 1.2 eq. assuming silane purity of 100%) was added scoopwise over 1 hour, followed by an additional hour of stirring while maintaining the temperature. The suspension was filtered and the solid rinsed with pentane (50 mL). Solvent was removed by rotary evaporation and the suspension again taken up in pentane (70 mL), and filtered through quantitative filter paper, that was then rinsed with additional pentane (50 mL). Removal of solvent by rotary evaporation yielded crude isopropenyldiisopropylbromosilane (15 g) as a hazy, pale brown liquid.

Workup

  1. temperaturecooled in an ice bath
  2. waitfollowed by an additional hour
  3. temperaturewhile maintaining the temperature
  4. filtrationThe suspension was filtered
  5. washthe solid rinsed with pentane (50 mL)
  6. customSolvent was removed by rotary evaporation
  7. filtrationfiltered through quantitative filter paper, that
  8. washwas then rinsed with additional pentane (50 mL)
  9. customRemoval of solvent
  10. customby rotary evaporation

Sources & evidence

ORD record
ord-429f42242c6b468da989cdb6fa9c48a7
Source dataset
uspto-grants-2014_07
Patent number
US08779179B2

Reaction notes

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