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

HRID 59332

Reaction equation

HRID 59332 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-649418e8072746319213417db71ea5ca
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Linked notes

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