Water → HCID 19362374, compound

HRID 850237Notes

Reaction equation

HRID 850237 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1Br.[CH3:20][Si:21]([C:24]#[CH:25])([CH3:23])[CH3:22].O>C(NCC)C.[Cu](I)I>[F:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[C:25]#[C:24][Si:21]([CH3:23])([CH3:22])[CH3:20]

Participants

6

Reactant 3

HCID 962WaterHCID 66111TrimethylsilylacetyleneHCID 193623862-Fluoro-4-[2-(4-propylphenyl)ethynyl]bromobenzene

Product 1

HCID 19362374HCID 19362374, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8021DiethylamineSolvent2×

Procedure

33 mmol of 2-fluoro-4-[2-(4-propylphenyl)ethynyl]bromobenzene, 1.2 mmol of copper iodide and 1.2 mmol of dichlorobistriphenylphosphine palladium were dissolved in 100 ml of diethylamine and the solution was stirred under an argon stream. To the reaction solution were added dropwise 20 ml of a diethylamine solution of 50 mmol of trimethylsilylacetylene and the solution was stirred at room -temperature for 5 hours. After completion of the agitation, water was added to the reaction solution which was extracted with heptane. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a brown oily product. This product was isolated and purified by a silica gel column chromatography to afford 7 g of 1-[2-fluoro-4-[2-(4-propylphenyl)ethynyl]phenyl]-2-trimethylsilylacetylene as a colourless solid.

Workup

  1. stirringthe solution was stirred at room -temperature for 5 hours
  2. extractionwas extracted with heptane
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto afford a brown oily product
  7. customThis product was isolated
  8. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-a792fa16ba72427c9297fdd49526266c
Source dataset
uspto-grants-2000_01
Patent number
US06017467

Reaction notes

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