Hydrochloric Acid → 2-Fluoro-4-[2-(4-propylphenyl)ethynyl]phenyl acetylene

HRID 850238Notes

Reaction equation

HRID 850238 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]=1[C:19]#[C:20][Si](C)(C)C.[OH-].[K+].Cl>C(O)C.O>[F:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][CH3:18])=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[C:19]#[CH:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19362374HCID 19362374, compound

Product 1

HCID 541902552-Fluoro-4-[2-(4-propylphenyl)ethynyl]phenyl acetyleneYield 98.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

22 mmol of 1-[2-fluoro-4-[2-(4-propylphenyl)-ethynyl]phenyl]-2-trimethylsilylacetylene and 10 g of potassium hydroxide were dissolved in 100 ml of ethanol and 10 ml of water, and the solution was stirred at 40° C. for 6 hours. After completion of the agitation, the reaction solution was poured into dilute hydrochloric acid and extracted with toluene. 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 5.7 g of 2-fluoro-4-[2-(4-propylphenyl)ethynyl]phenyl acetylene as a colourless solid.

Workup

  1. extractionextracted with toluene
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto afford a brown oily product
  6. customThis product was isolated
  7. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-d0fed464de92498abc6c0adac68762f7
Source dataset
uspto-grants-2000_01
Patent number
US06017467

Reaction notes

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