Triethylamine → (4-Chlorophenylethynyl)trimethylsilane

HRID 1199594Notes

Reaction equation

HRID 1199594 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18].[Cl-].[NH4+]>C(#N)C.[Cu](I)I.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.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 125101-Chloro-4-iodobenzeneHCID 25517Ammonium ChlorideHCID 66111Trimethylsilylacetylene

Product 1

HCID 3337298(4-Chlorophenylethynyl)trimethylsilaneYield 93.4%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4-chloroiodobenzene (4.77 g:0.02 mole) in dry acetonitrile (30 ml) and triethylamine (2.02 g:0.02 mole) under nitrogen, was added copper iodide (0.2 g:1.05 mole), bis (triphenylphosphine)palladium dichloride (0.2 g=0.285 mmole) and trimethylsilylethyne (2.156 g:0.022 mole). The mixture was stirred for three hours during which time there was an exotherm at 20° C. and a darkening of the reacton mixture. The mixture was poured into saturated ammonium chloride solution (100 ml) and was extracted with ether (×3). The extracts were combined, washed with dilute hydrochloric acid and dried over magnesium sulfate and then filtered through charcoal. Removal of solvent in vacuo gave a brown oil which was titurated with hexane and filtered to remove by-products. The filtrate was evaporated to give yellow crystals (3.90 g).

Workup

  1. customat 20° C.
  2. extractionwas extracted with ether (×3)
  3. washwashed with dilute hydrochloric acid
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through charcoal
  6. customRemoval of solvent in vacuo
  7. customgave a brown oil which
  8. filtrationfiltered
  9. customto remove by-products
  10. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-ea74fe9d39b449a4ac066e630643b61a
Source dataset
uspto-grants-1990_02
Patent number
US04902332

Reaction notes

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