Phenylacetylene → 1-Methoxy-4-(phenylethynyl)benzene

HRID 1776058Notes

Reaction equation

HRID 1776058 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)#[CH:2].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1>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>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 10821PhenylacetyleneHCID 696764-Iodoanisole

Product 1

HCID 6104021-Methoxy-4-(phenylethynyl)benzeneYield 97%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

112 mg (1.1 mmol) of ethynylbenzene, 259 mg (1.1 mmol) of 4-methoxy-iodobenzene, 2 mg (10 μmol) of cupric iodide and 8 mg (10 μmol) of bis(triphenylphosphine)palladium(II) chloride were added to a round-bottomed flask. The round-bottomed flask was then purged 3 times with argon. 20 ml of distilled triethylamine were then added and the mixture was then stirred for 24 hours. The reaction medium was then diluted with 20 ml of a 6M solution of hydrochloric acid then extracted three times with 20 ml of dichloromethane. The organic phase was washed with 40 ml of a 1M solution of sodium hydroxide, then dried over sodium sulfate and the solvent was evaporated under reduced pressure. The crude product of the reaction was then purified by column chromatography using, as eluent, a petroleum ether/dichloromethane (7/3; v/v) mixture. The expected product was then isolated in the form of a yellow powder (m=201 mg; yield=97%).

Workup

  1. customThe round-bottomed flask was then purged 3 times with argon
  2. addition20 ml of distilled triethylamine were then added
  3. additionThe reaction medium was then diluted with 20 ml of a 6M solution of hydrochloric acid
  4. extractionthen extracted three times with 20 ml of dichloromethane
  5. washThe organic phase was washed with 40 ml of a 1M solution of sodium hydroxide
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe crude product of the reaction was then purified by column chromatography

Sources & evidence

ORD record
ord-c5f2ae1e9ca841c5a2bebce4bd7fdf7e
Source dataset
uspto-grants-2016_02
Patent number
US09263683B2

Reaction notes

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