Trimethylsilylacetylene → ((4-Chloro-2-fluorophenyl)ethynyl)trimethylsilane

HRID 508825Notes

Reaction equation

HRID 508825 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([F:9])[CH:3]=1.[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])#[CH:11]>CS(C)=O.[Cu](I)I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]#[C:10][Si:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([F:9])[CH:3]=1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 27365624-Chloro-2-fluoro-1-iodobenzene

Product 1

HCID 90019293((4-Chloro-2-fluorophenyl)ethynyl)trimethylsilaneYield 56.5%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-chloro-2-fluoro-1-iodobenzene (2.0 g, 7.8 mmol) in DMSO (10 mL) was added ethynyl(trimethyl)silane (1.14 g, 11.0 mmol), copper iodide (0.029 g, 0.15 mmol), bis(triphenylphosphine) palladium(II) chloride (0.218 g, 0.3 mmol) and TEA (1 mL). The reaction mass was stirred at RT for 4-5 h. The reaction mass quenched in water, passed through celite bed and extracted with ethyl acetate and concentrated to afford 1.0 g of desired product.

Workup

  1. customThe reaction mass quenched in water
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-138134a5f9054324b8f30cc060a031ea
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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