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

HRID 1199084Notes

Reaction equation

HRID 1199084 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.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[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

5

Reactant 2

HCID 10821Phenylacetylene3×HCID 27340921-(2-Bromophenyl)propan-2-one

Product 1

HCID 139106162-[(Phenyl)ethynyl]phenyl-2-propanoneYield 59%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst2×HCID 8471TriethylamineSolvent2×

Procedure

To a 3-necked, round bottom flask under nitrogen was added 4.0 g (18.8 mmole) of 2-bromophenyl-2-propanone in 40 ml of triethylamine, 2.5 ml (22.5 mmole) of phenylacetylene, 0.3 g (2 mole %) of bis-(triphenylphosphine) palladium dichloride and 0.14 g (4 mole %) of cuprous iodide. After refluxing for three hours another 0.5 ml (4.5 mmole) of phenylacetylene, 0.6 g (4 mole %) of bis (triphenylphosphine) palladium dichloride and 0.3 g (8 mole %) of cuprous iodide were added. Reflux was continued another 11/2 hours before 1.0 ml (9.0 mmole) of phenylacetylene and 10 ml of triethylamine were added. After an additional 21/2 hours at reflux the reaction was partitioned between ether and water, washed with brine, dried over MgSO4 and evaporated in vacuo to yield 55 g of crude reaction product. The mixture was flash chromatographed eluting with 1:19 ethyl acetate:hexane to give 2.6 g (59%) of 2-(phenylethynyl)phenyl-2-propanone as a dark oil.

Workup

  1. additionwere added
  2. temperatureReflux
  3. custom2 hours
  4. additionwere added
  5. temperatureAfter an additional 21/2 hours at reflux the reaction
  6. customwas partitioned between ether and water
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. customevaporated in vacuo
  10. customto yield 55 g of crude
  11. customreaction product
  12. customchromatographed
  13. washeluting with 1:19 ethyl acetate

Sources & evidence

ORD record
ord-b3e2716768774897876ba64bef06b0c3
Source dataset
uspto-grants-1990_02
Patent number
US04898889

Reaction notes

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