Phenylacetylene → 2-[(Phenyl)ethynyl]phenyl-2-propanone

HRID 543436Notes

Reaction equation

HRID 543436 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[O:11])[CH3:10].[C:12]1([C:18]#[CH:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[C:12]1([C:18]#[C:19][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][C:9](=[O:11])[CH3:10])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 10821Phenylacetylene4×HCID 27340921-(2-Bromophenyl)propan-2-one

Product 1

HCID 139106162-[(Phenyl)ethynyl]phenyl-2-propanoneYield 81%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst3×HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 28.3 g (112 mmole) of 2-bromophenyl-2-propanone, 14.7 ml (134 mmole) of phenylacetylene, 1.8 g (2.24 mmole) of bis(triphenylphosphine)palladium (II) chloride and 0.85 g (4.48 mmole) of copper (I) iodide in 250 ml of triethylamine under nitrogen was heated under reflux for 31/2 hours. An additional 3.6 ml of phenylacetylene, 0.36 g of palladium complex and 0.1 g copper (I) iodide were added. The mixture was heated under reflux for 31/2 hours. An additional 5.0 ml of phenylacetylene, 0.36 g of palladium complex and 0.17 g of copper (I) iodide were added. The mixture was heated under reflux for 2 hours. An additional 5.0 ml of phenylacetylene was added. The mixture was heated under reflux for 31/2 hours. The solvent was evaporated in vacuo and the residue taken up in ether. The ether was washed with water and brine, dried (K2CO3) and the solvent evaporated in vacuo. The residue was flash chromatographed on silica gel with ethyl acetate:hexane, 9:1, as eluant. The solvent was evaporated from the major compound bearing fraction to afford 21.2 g (81% yield) of 1-[2-(phenylethynyl)phenyl]-2-propanone as an oil.

Workup

  1. temperatureunder reflux for 31/2 hours
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 31/2 hours
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 2 hours
  6. temperatureThe mixture was heated
  7. temperatureunder reflux for 31/2 hours
  8. customThe solvent was evaporated in vacuo
  9. washThe ether was washed with water and brine
  10. dry with materialdried (K2CO3)
  11. customthe solvent evaporated in vacuo
  12. customchromatographed on silica gel with ethyl acetate
  13. customThe solvent was evaporated from the major compound bearing fraction

Sources & evidence

ORD record
ord-8b2cbad8755d4380ab4ca11eeaff8a4b
Source dataset
uspto-grants-1987_04
Patent number
US04661635

Reaction notes

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