Bromide ion → HCID 86652237, compound

HRID 2407603Notes

Reaction equation

HRID 2407603 reaction equation
[CH3:1][Si:2]([C:5]#[C:6][SiH:7]([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])([CH3:4])[CH3:3].[Br-:14]>Cl[Pd]Cl.C(Br)C=C>[CH3:4][Si:2]([C:5]#[C:6][Si:7]([CH:11]([CH3:13])[CH3:12])([CH:8]([CH3:9])[CH3:10])[Br:14])([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 259Bromide ionHCID 101337817HCID 101337817, compound

Product 1

HCID 86652237HCID 86652237, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 7841Allyl bromideSolvent

Conditions

Temperature
60 °C

Procedure

(Trimethylsilylethynyl)diisopropylsilane (14 g, 66 mmol) and allyl bromide (˜40 mL) were added to a round-bottom flask equipped with a stir-bar. A septum and bubbler were attached and the solution was purged with N2 for 15 min. PdCl2 (0.06 g, 0.3 mmol, 0.5 mol %) was added and the reaction was heated at 60° C. for 3 hours, or until analysis by GC-MS showed complete conversion to the bromide. After removing the reaction from the heat, pentane (50 mL) was added and the solution was chilled for 20 min. The PdCl2 was removed by filtration through a fine fitted funnel, then solvent was removed using a rotary evaporator, yielding 18.8 g of (trimethylsilylethynyl)diisopropylbromosilane as a light brown liquid.

Workup

  1. customequipped with a stir-bar
  2. customthe solution was purged with N2 for 15 min
  3. customAfter removing
  4. customthe reaction from the heat, pentane (50 mL)
  5. additionwas added
  6. temperaturethe solution was chilled for 20 min
  7. customThe PdCl2 was removed by filtration through a fine fitted funnel
  8. customsolvent was removed
  9. customa rotary evaporator

Sources & evidence

ORD record
ord-df19251f67504e879297feadbfe5ceec
Source dataset
uspto-grants-2014_08
Patent number
US08809568B2

Reaction notes

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