p-Iodocumene → 1,2-Bis(4-(2-propyl)phenyl)acetylene

HRID 378245Notes

Reaction equation

HRID 378245 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].I[C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH: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>[CH3:2][CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]#[C:11][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[CH:8][CH:9]=1)[CH3:3]

Participants

6

Reactant 2

HCID 87073p-IodocumeneHCID 6375011-Ethynyl-4-(1-methylethyl)benzene

Product 1

HCID 112540441,2-Bis(4-(2-propyl)phenyl)acetyleneYield 87%

Reagents, catalysts & solvents 3

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

Procedure

The crude 4-isopropylphenylacetylene was dissolved in triethylamine (100 mL). 4-iodoisopropylbenzene (12.3 g, 50 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.70 g, 1 mmol), and copper(I) iodide (1.5 g) were added. The reaction was stirred at room temperature for 2 days, heated to reflux for 1 hour, cooled, diluted with hexanes, and filtered. The filtrate was evaporated under reduced pressure. The residue was filtered through a pad of silica gel with hexanes, and the solvent was evaporated to give 11.40 g (87%) of 1,2-bis(4-(2-propyl)phenyl)acetylene.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. filtrationThe residue was filtered through a pad of silica gel with hexanes
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-86611bb695494aedb40a1dd31ddf11da
Source dataset
uspto-grants-2000_02
Patent number
US06030969

Reaction notes

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