1-Ethynyl-4-propylbenzene → 2-Fluoro-4-[2-(4-propylphenyl)ethynyl]bromobenzene

HRID 931846Notes

Reaction equation

HRID 931846 reaction equation
[Br:1][C:2]1[C:3]([F:10])=[CH:4][C:5](I)=[C:6](C)[CH:7]=1.[CH2:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]#[CH:21])=[CH:16][CH:15]=1)[CH2:12][CH3:13]>C(NC(C)C)(C)C.[Cu]I>[CH2:11]([C:14]1[CH:15]=[CH:16][C:17]([C:20]#[C:21][C:5]2[CH:4]=[C:3]([F:10])[C:2]([Br:1])=[CH:7][CH:6]=2)=[CH:18][CH:19]=1)[CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 27751331-Ethynyl-4-propylbenzeneHCID 121872165-Bromo-4-fluoro-2-iodotoluene

Product 1

HCID 193623862-Fluoro-4-[2-(4-propylphenyl)ethynyl]bromobenzene

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 7912DiisopropylamineSolvent

Procedure

20 g (63.5 mmol) of 5-bromo-4-fluoro-2-iodotoluene, 10.5 g (73 mmol) of 4-n-propylphenylacetylene, 2.5 g (3.6 mmol) of bis(triphenylphosphine)palladium-(II) chloride and 300 mg (1.8 mmol) of copper(I) iodide are initially introduced in 250 ml of diisopropylamine, the mixture is heated under reflux for 3 h and cooled, and the precipitate formed is filtered off. The filtrate is evaporated in a rotary evaporator, and the residue obtained in this way is purified by column chromatography (SiO2, heptane).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 h
  3. temperaturecooled
  4. customthe precipitate formed
  5. filtrationis filtered off
  6. customThe filtrate is evaporated in a rotary evaporator
  7. customthe residue obtained in this way
  8. customis purified by column chromatography (SiO2, heptane)

Sources & evidence

ORD record
ord-93f074bb3bc94a24be837e90e6d6fcc9
Source dataset
uspto-grants-2016_03
Patent number
US09296948B2

Reaction notes

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