Water → 1-(4-n-Butylphenylethynyl)-4-(4-n-propylphenylethynyl)naphthalene

HRID 403067Notes

Reaction equation

HRID 403067 reaction equation
BrC1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH3:22])=[CH:16][CH:15]=2)=[CH:4]C=1.[CH2:23]([C:27]1[CH:32]=[CH:31][C:30]([C:33]#[CH:34])=[CH:29][CH:28]=1)[CH2:24][CH2:25][CH3:26].O.[CH3:36][CH2:37]CCCCC>CCN(CC)CC.[Cu]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>[CH2:33]([C:30]1[CH:29]=[CH:28][C:27]([C:23]#[C:24][C:25]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][CH3:22])=[CH:18][CH:19]=3)=[CH:4][CH:26]=2)=[CH:32][CH:31]=1)[CH2:34][CH2:36][CH3:37]

Participants

8

Reactant 4

HCID 962WaterHCID 8900HeptaneHCID 27751321-Butyl-4-ethynylbenzeneHCID 671178511-Bromo-4-(4-n-propylphenylethynyl)naphthalene

Product 1

HCID 867624711-(4-n-Butylphenylethynyl)-4-(4-n-propylphenylethynyl)naphthalene

Reagents, catalysts & solvents 3

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

Procedure

2.35 g (6.3 mmol) of 1-bromo-4-(4-n-propylphenylethynyl)naphthalene and 1.33 g (8.4 mmol) of 4-n-butylphenylacetylene are initially introduced in 40 ml of NEt3, 60 mg (0.3 mmol) of copper(I) iodide and 200 mg (0.3 mmol) of bis(triphenylphosphine)palladium(II) chloride are added, and the mixture is refluxed for 18 h. The batch is cooled, water and heptane are added, and the phases are separated. The organic phase is washed with saturated ammonium chloride solution and subsequently with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated in a rotary evaporator. The residue of compound (1) is purified by column chromatography (SiO2, heptane), and the further purification is carried out by recrystallisation from isopropanol.

Workup

  1. temperaturethe mixture is refluxed for 18 h
  2. temperatureThe batch is cooled
  3. customthe phases are separated
  4. washThe organic phase is washed with saturated ammonium chloride solution and subsequently with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in a rotary evaporator
  8. customThe residue of compound (1) is purified by column chromatography (SiO2, heptane)
  9. customthe further purification
  10. customis carried out by recrystallisation from isopropanol

Sources & evidence

ORD record
ord-c8d6a1e4633540f19073da98de7a307e
Source dataset
uspto-grants-2014_06
Patent number
US08747695B2

Reaction notes

Loading…