Trimethylsilylacetylene → HCID 12579657, compound

HRID 1086789Notes

Reaction equation

HRID 1086789 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(NCC)C>[CH3:15][Si:16]([C:19]#[C:20][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1)([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 763484,4'-Diiodo-1,1'-biphenyl

Product 1

HCID 12579657HCID 12579657, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

In a flask having its atmosphere completely displaced with nitrogen were charged 19 g of 4,4'-diiodobiphenyl, 1.31 g of bis(triphenylphosphine)palladium dichloride, 0.094 g of cuprous iodide and 500 ml of diethylamine. The temperature was elevated to 30° C. under stirring, and 11.04 g of trimethylsilylacetylene was added to the mixture, followed by allowing the mixture to react for 4.5 hours to obtain 4,4'-di(trimethylsilylethynyl)biphenyl. Hydrolysis of this product yielded 4,4'-diethynylbiphenyl.

Workup

  1. customIn a flask having
  2. customwas elevated to 30° C.
  3. customto react for 4.5 hours

Sources & evidence

ORD record
ord-9f58f32519a045d78c7ff6d796f6553c
Source dataset
uspto-grants-1991_07
Patent number
US05032489

Reaction notes

Loading…