Trimethylsilylacetylene → [(2,3-Dichlorophenyl)ethynyl](trimethyl)silane

HRID 2232964Notes

Reaction equation

HRID 2232964 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[C:3]=1[Cl:9].[CH3:10][Si:11]([C:14]#[CH:15])([CH3:13])[CH3:12]>C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[Cl:9][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[C:15]#[C:14][Si:11]([CH3:13])([CH3:12])[CH3:10]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 754591,2-Dichloro-3-iodobenzene

Product 1

HCID 69198883[(2,3-Dichlorophenyl)ethynyl](trimethyl)silane

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

1,2-Dichloro-3-iodobenzene (4.95 g, 18.1 mmol), trimethylsilylacetylene (2 g, 20 mmol), bis(triphenylphosphine)palladium(II)chloride (245 mg, 0.35 mmol), and copper(I)iodide (45 mg, 0.24 mmol) were combined in triethylamine (120 mL) and heated at reflux for 45 minutes. The mixture was allowed to cool to room temperature and was then partitioned between diethyl ether and saturated sodium chloride. The organic phase was dried with sodium sulfate, filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was taken directly on to the next step.

Workup

  1. temperatureheated
  2. temperatureat reflux for 45 minutes
  3. customwas then partitioned between diethyl ether and saturated sodium chloride
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. filtrationfiltered through celite
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7d7ee3507aef4eb1b1de0440e10cbfe9
Source dataset
uspto-grants-2010_05
Patent number
US07709469B2

Reaction notes

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