4-Iodophenol → 4-[2-(4-Methylphenyl)ethynyl]phenol

HRID 565156Notes

Reaction equation

HRID 565156 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1)#[CH:2].I[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cu](I)I.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(N(CC)CC)C>[C:6]1([CH3:9])[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:4][CH:5]=1

Participants

7

Reactant 3

HCID 108944-IodophenolHCID 11776TriphenylphosphineHCID 13018p-Ethynyltoluene

Product 1

HCID 187390274-[2-(4-Methylphenyl)ethynyl]phenol

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst3×HCID 8471TriethylamineSolvent

Procedure

50 g of 4-ethynyltoluene, 94.6 g of 4-iodophenol and 250 ml of triethylamine were mixed at RT under a nitrogen atmosphere, and 0.35 g of triphenylphosphine and 0.2 g of copper iodide were added. 0.25 g of bis(triphenylphosphine)palladium(II) chloride were then introduced with stirring. After 30 minutes, a further 0.25 g of bis(triphenylphosphine)palladium(II) chloride and after a further 15 minutes a further 0.25 g of bis(triphenylphosphine)palladium(II) chloride were introduced, during which the temperature was held at between 40 and 55° C. After the reaction mixture had been stirred overnight, it was poured into conc. HCl/ice and subjected to conventional work-up, giving 4-p-tolylethynylphenol in the form of a solid.

Workup

  1. customwas held at between 40 and 55° C
  2. stirringAfter the reaction mixture had been stirred overnight

Sources & evidence

ORD record
ord-5d10583b1c9e40a3bec476305c6af49c
Source dataset
uspto-grants-2001_01
Patent number
US06171664B2

Reaction notes

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