Trimethylsilylacetylene → Tris(4-((trimethylsilyl)ethynyl)phenyl)amine

HRID 1840694Notes

Reaction equation

HRID 1840694 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25]>[Cu](I)I.C(NC(C)C)(C)C>[CH3:23][Si:24]([C:27]#[C:28][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[CH:21]=[CH:20][C:19]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1)([CH3:26])[CH3:25]

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 258027Tris(4-bromophenyl)amine

Product 1

HCID 23443707Tris(4-((trimethylsilyl)ethynyl)phenyl)amineYield 81%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 7912DiisopropylamineSolvent

Procedure

Thereafter, to 200 ml of diisopropylamine were added 15.54 g (0.032 mol of tri(4-bromophenyl)amine, 1.35 g (1.92 mmol) of bis[triphenylphosphin]palladium dichloride and 9.43 g (0.96 mmol) of copper iodide. After the reaction mixture was stirred for 2 h at room temperature, 9.43 g, (96 mmol) of trimethylsilyl acetylene was slowly added to the reaction mixture. The reaction mixture was refluxed for 8 h and cooled. Solvent was removed under the reduced pressure. The residue was extracted with benzene and the benzene layer was washed with distilled water. The washed benzene layer was concentrated to give 13.84 g (81%) of tri(4-trimethylsilylethynylphenyl)amine.

Workup

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. temperaturecooled
  3. customSolvent was removed under the reduced pressure
  4. extractionThe residue was extracted with benzene
  5. washthe benzene layer was washed with distilled water
  6. concentrationThe washed benzene layer was concentrated

Sources & evidence

ORD record
ord-c28251a72e284fd682b010ce47b24c90
Source dataset
uspto-grants-2004_01
Patent number
US06682782B2

Reaction notes

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