Water → 1,2-Bis(4-methoxyphenyl)ethyne

HRID 1760090Notes

Reaction equation

HRID 1760090 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1)#[CH:2].I[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.C(NC(C)C)(C)C.O>C1COCC1.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.[Cu]I>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:4][CH:5]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7912DiisopropylamineHCID 696764-IodoanisoleHCID 2510201-Ethynyl-4-methoxybenzene

Product 1

HCID 6172341,2-Bis(4-methoxyphenyl)ethyneYield 95%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-ethynylanisole (700 mg, 5.30 mmol), 4-iodoanisole (1.30 g, 5.55 mmol), (PPh3)2PdCl2 (74.4 mg, 0.106 mmol), and CuI (10.1 mg, 0.053 mmol) in THF (7 ml), diisopropyl amine (1.13 g, 11.1 mmol) was added dropwise under ice cooling under argon atmosphere. After stirring at room temperature for 1 h, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water then saturated brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=15/1) to give bis(4-methoxyphenyl)ethyne (95%).

Workup

  1. additionwas added dropwise under ice cooling under argon atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialsaturated brine, dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-8e354f6f47b9491e8ee9038da2c0a51a
Source dataset
uspto-grants-2005_01
Patent number
US06838574B1

Reaction notes

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