Phenylacetylene → HCID 46224400, compound

HRID 2369444Notes

Reaction equation

HRID 2369444 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].[C:13]1([C:19]#[CH:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(N(CC)CC)C.[Cu](I)I>[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:20]#[C:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([F:4])[F:3]

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 69670677HCID 69670677, compound

Product 1

HCID 46224400HCID 46224400, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8471TriethylamineSolvent2×

Procedure

A suspension of PdCl2PPH3 (0.027 g, 0.063 mmol) and copper iodide (0.0035 g, 0.018 mmol) in 3 ml of triethylamine was charged into a 50-ml eggplant flask equipped with a stirrer. To this suspension, a solution of (trifluoromethyl)(2-iodophenyl)sulfide (0.57 g, 1.9 mmol) prepared in Example 1 and phenylacetylene (0.23 g, 2.2 mmol) in 2 ml of triethylamine was added dropwise at room temperature, and the mixture was stirred overnight. After completion of the reaction, a solvent was removed, water was added to the obtained residue, and the mixture was extracted three times with ether. The obtained organic layers was collected and washed with water, dried over anhydrous sodium sulfate, and concentrated to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (Benzen/Hexane=20/80) to give target (trifluoromethyl)-(2-(2-phenylethynyl)phenyl)sulfide (0.5 g, 96%).

Workup

  1. additionwas charged into a 50-ml eggplant flask
  2. customequipped with a stirrer
  3. customAfter completion of the reaction
  4. customa solvent was removed
  5. additionwater was added to the obtained residue
  6. extractionthe mixture was extracted three times with ether
  7. customThe obtained organic layers was collected
  8. washwashed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customto obtain a crude product
  12. customThe obtained crude product
  13. customwas purified by silica gel column chromatography (Benzen/Hexane=20/80)

Sources & evidence

ORD record
ord-393d15d1ebf24769841938714b011bcd
Source dataset
uspto-grants-2014_04
Patent number
US08703969B2

Reaction notes

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