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

HRID 403066

Reaction equation

HRID 403066 reaction equation
I[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Br:12])=[CH:4][CH:3]=1.[CH2:13]([C:16]1[CH:21]=[CH:20][C:19]([C:22]#[CH:23])=[CH:18][CH:17]=1)[CH2:14][CH3:15].O.CCCCCCC>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>[Br:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:23]#[C:22][C:19]2[CH:20]=[CH:21][C:16]([CH2:13][CH2:14][CH3:15])=[CH:17][CH:18]=2)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8900HeptaneHCID 27751331-Ethynyl-4-propylbenzeneHCID 50736671-Bromo-4-iodonaphthalene

Product 1

HCID 671178511-Bromo-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

15.3 g (43.6 mmol) of 1-iodo-4-bromonaphthalene and 7.25 g (5.3 mmol) of 4-n-propylphenylacetylene are initially introduced in 200 ml of NEt3, 170 mg (0.9 mmol) of copper(I) iodide and 600 mg (0.9 mmol) of bis-(triphenylphosphine)palladium(II) chloride are added, and the mixture is refluxed for 30 minutes. The batch is cooled, water and heptane are added, and the phases are separated. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated in a rotary evaporator. The residue 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 30 minutes
  2. temperatureThe batch is cooled
  3. customthe phases are separated
  4. washThe organic phase is washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in a rotary evaporator
  8. customThe residue is purified by column chromatography (SiO2, heptane)
  9. customthe further purification
  10. customis carried out by recrystallisation from isopropanol

Sources & evidence

ORD record
ord-4ceefc20bc9a4030bd16717248086541
Source dataset
uspto-grants-2014_06
Patent number
US08747695B2

Linked notes

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