Phenylacetylene → HCID 20481558, compound

HRID 1648720Notes

Reaction equation

HRID 1648720 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14](I)[C:13]([Cl:17])=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][N:7]([CH2:10][CH3:11])[CH2:8][CH3:9].[C:18]1([C:24]#[CH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(N(CC)CC)C.[Pd].[Cu]I>[Cl:1][C:2]1[CH:15]=[C:14]([C:25]#[C:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]([Cl:17])=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][N:7]([CH2:10][CH3:11])[CH2:8][CH3:9]

Participants

7

Reactant 3

HCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 20481567HCID 20481567, compound

Product 1

HCID 20481558HCID 20481558, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 19.4 g (0.05 mole) of 1-(2,5-dichloro-4-iodophenoxy)-2-diethylaminoethane and 5.2 g (0.053 mole) of phenylacetylene in 250 ml of triethylamine are added, under nitrogen, 200 mg of the palladium complex PdCl2 [P(C6H5)3 ]2 and 100 mg of copper(I) iodide. After the weakly exothermic reaction has subsided, the reaction mixture is stirred for 15 hours at room temperature, then concentrated, and the residue is taken up in water. After extraction with 200 ml of ether, the combined ethereal phases are washed 4 times with water, dried and evaporated to dryness. The crude product is chromatographed on silica gel, affording 14.3 g (79%) of 1-(2,5-dichloro-4-phenylethynylphenoxy)-2-diethylaminoethane with a refractive index of nD25 :1.6173.

Workup

  1. customAfter the weakly exothermic reaction
  2. concentrationconcentrated
  3. extractionAfter extraction with 200 ml of ether
  4. washthe combined ethereal phases are washed 4 times with water
  5. customdried
  6. customevaporated to dryness
  7. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-bd893f59552e40cb9a1e7664d1dbe57a
Source dataset
uspto-grants-1983_11
Patent number
US04412856

Reaction notes

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