Cyclopropylacetylene → HCID 69670549, compound

HRID 2369441Notes

Reaction equation

HRID 2369441 reaction equation
[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1I)([F:4])[F:3].[CH:13]1([C:16]#[CH:17])[CH2:15][CH2:14]1>C(N(CC)CC)C.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.[Cu]I>[CH:13]1([C:16]#[C:17][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:2]([F:4])([F:3])[F:1])[CH2:15][CH2:14]1

Participants

6

Reactant 2

HCID 138823CyclopropylacetyleneHCID 69670677HCID 69670677, compound

Product 1

HCID 69670549HCID 69670549, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent2×

Procedure

Bis(triphenylphosphine)palladium(II) dichloride ([(C6H5)3P]2PdCl2, 0.0518 g, 5 mol %), copper(I) iodide (0.0086 g, 3 mol %), and triethylamine (3 ml) were charged into a 25-ml round-bottomed flask equipped with a stirrer, and were suspended by stirring at room temperature. To the suspension, a solution obtained by dissolving 2-trifluoromethylsulfanyliodobenzene (1.08 g, 3.6 mmol) prepared in Reference Example 1 and cyclopropylacetylene (0.35 g, 5.3 mmol) in triethylamine (2 ml) was added dropwise, and the solution was stirred at room temperature overnight. After completion of the reaction, a solvent was removed under reduced pressure, and water was added to the obtained residue. The solution was extracted with ether, and the organic layers were combined together, washed with water, dried over magnesium sulfate, filtered, and concentrated to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (hexane) to give target 1-cyclopropylethynyl-2-trifluoromethylsulfanylbenzene (0.67 g, yield: 78%) as an oil.

Workup

  1. customequipped with a stirrer
  2. customTo the suspension, a solution obtained
  3. additionwas added dropwise
  4. stirringthe solution was stirred at room temperature overnight
  5. customAfter completion of the reaction
  6. customa solvent was removed under reduced pressure, and water
  7. additionwas added to the obtained residue
  8. extractionThe solution was extracted with ether
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto obtain a crude product
  14. customThe obtained crude product
  15. customwas purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-2c273257a884400bb5cdbf5ff86f349f
Source dataset
uspto-grants-2014_04
Patent number
US08703969B2

Reaction notes

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