Water → HCID 86708837, compound

HRID 931847Notes

Reaction equation

HRID 931847 reaction equation
I[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5](I)=[C:4]([CH3:11])[C:3]=1[CH3:12].[CH2:13]([C:17]1[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[CH:19][CH:18]=1)[CH2:14][CH2:15][CH3:16].O>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.[Cu]I>[CH2:13]([C:17]1[CH:18]=[CH:19][C:20]([C:23]#[C:24][C:2]2[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([C:24]#[C:23][C:20]3[CH:21]=[CH:22][C:17]([CH2:13][CH2:14][CH2:15][CH3:16])=[CH:18][CH:19]=3)=[C:4]([CH3:11])[C:3]=2[CH3:12])=[CH:21][CH:22]=1)[CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 3

HCID 962WaterHCID 27751321-Butyl-4-ethynylbenzeneHCID 51825261,4-Diiodo-2,3,5,6-tetramethylbenzene

Product 1

HCID 86708837HCID 86708837, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

8.1 g (20 mmol) of 1,4-diiodo-2,3,5,6-tetramethylbenzene, 7.5 g (47.3 mmol) of 4-n-butylphenylacetylene, 2 g (2.9 mmol) of bis(triphenylphosphine)palladium(II) chloride and 550 mg (2.9 mmol) of copper(I) iodide are initially introduced in 100 ml of triethylamine, and the mixture is heated under reflux for 3 h. The batch is then cooled, water and MTB are added, and the phases are separated. The organic phase is washed with saturated ammonium chloride solution and with sodium chloride solution and evaporated in a rotary evaporator, and the residue obtained in this way is purified by column chromatography (SiO2, heptane); the further purification is carried out by recrystallisation from isopropanol.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 h
  3. temperatureThe batch is then cooled
  4. customthe phases are separated
  5. washThe organic phase is washed with saturated ammonium chloride solution and with sodium chloride solution
  6. customevaporated in a rotary evaporator
  7. customthe residue obtained in this way
  8. customis purified by column chromatography (SiO2, heptane)
  9. customthe further purification
  10. customis carried out by recrystallisation from isopropanol

Sources & evidence

ORD record
ord-c92f1bacd1ee495a837d61c0ccf58dc1
Source dataset
uspto-grants-2016_03
Patent number
US09296948B2

Reaction notes

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