Phenylacetylene → HCID 21705263, compound

HRID 1739363Notes

Reaction equation

HRID 1739363 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14](Br)[CH:13]=2)=[O:11])=[O:9])[CH:5]=[CH:6][CH:7]=1.[C:19]1([C:25]#[CH:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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>[C:19]1([C:25]#[C:26][C:2]2[CH:3]=[C:4]([C:8]([C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:10]#[C:8][C:4]4[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=4)[CH:13]=3)=[O:11])=[O:9])[CH:5]=[CH:6][CH:7]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 13789611HCID 13789611, compound

Product 1

HCID 21705263HCID 21705263, compoundYield 131.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 3,3'-dibromobenzil (5.0 g, 0.0136 mol) and phenylacetylene (3.47 g, 0.0340 mol) in triethylamine (30 mL) is deaerated by bubbling nitrogen through the solution for ten minutes. (PPh3)2PdCl2 (0.067 g, 0.0001 mol) is then added, and the reaction mixture heated at reflux overnight. The mixture is concentrated to dryness, then taken up in CH2Cl2 (100 mL), washed sequentially with 1 M HCl, saturated aqueous NaHCO3 and dried (Na2SO4), then concentrated, giving 3.67 g (66 percent) product as a white solid: m.p. 144° C. to 145° C.; 1H NMR (CDCl3) δ 8.12 (s, 2H), 7.96 (d, J=7.9 Hz, 2H), 7.81 (d, J=7.7 Hz, 2H), 7.52 (m, 6H), 7.36 (m, 6H); 13C NMR (CDCl3) δ 192.83, 137.40, 132.82, 131.52, 129.04, 128.58, 128.25, 124.50, 122.37, 91.11, 87.62.

Workup

  1. customby bubbling nitrogen through the solution for ten minutes
  2. temperaturethe reaction mixture heated
  3. temperatureat reflux overnight
  4. concentrationThe mixture is concentrated to dryness
  5. washwashed sequentially with 1 M HCl, saturated aqueous NaHCO3
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7dd5b0e03d0e4d4b9d8931f5dd87c512
Source dataset
uspto-grants-1999_10
Patent number
US05965679

Reaction notes

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