Trimethylsilylacetylene → HCID 71115286, compound

HRID 468854Notes

Reaction equation

HRID 468854 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1I.[CH3:10][Si:11]([C:14]#[CH:15])([CH3:13])[CH3:12].C(N(CC)C(C)C)(C)C>O1CCOCC1.C(OCC)C.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:15]#[C:14][Si:11]([CH3:13])([CH3:12])[CH3:10]

Participants

7

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 27562471-chloro-4-fluoro-2-iodobenzene

Product 1

HCID 71115286HCID 71115286, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-chloro-4-fluoro-2-iodobenzene (10 g, 40 mmol), (trimethylsilyl)acetylene (28 mL, 190 mmol), copper(I) iodide (740 mg, 3.9 mmol), (triphenylphosphine)palladium(0) (2.5 g, 2.2 mmol), and N,N-diisopropylethylamine (14 mL, 78 mmol) in 1,4-dioxane (100 mL) was heated at 90° C. for 2 hours. The cooled reaction mixture was then diluted with diethyl ether (200 mL) and washed with water (300 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 220 g, ISCO, heptane) to afford the title compound as a pale yellow oil (5 g, 60%), which was used in the next step without further purification.

Workup

  1. customThe cooled reaction mixture
  2. washwashed with water (300 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a residue that
  8. customwas purified by flash chromatography (silica, 220 g, ISCO, heptane)

Sources & evidence

ORD record
ord-2dae0f55639746b19d92c1ce5da01ba2
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

Loading…