Hydrochloric Acid → HCID 178447865, compound

HRID 850231Notes

Reaction equation

HRID 850231 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:11]2[CH2:16][CH2:15][C@H:14]([CH2:17][CH2:18][CH3:19])[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[C:8]#[C:9]I.[Cu](C#N)[C:21]#[N:22].[Br-].[Li+].Cl>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C@H:11]2[CH2:16][CH2:15][C@H:14]([CH2:17][CH2:18][CH3:19])[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[C:8]#[C:9][C:21]#[N:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 82050Lithium BromideHCID 178418260HCID 178418260, compoundHCID 178447871HCID 178447871, compound

Product 1

HCID 178447865HCID 178447865, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10 mmol of 3-fluoro-4-iodoethynyl-1-(trans-4-propylcyclohexyl)benzene in 3 ml of tetrahydrofuran were added 11 mmol of copper cyanide and 3 mmol of lithium bromide, and the solution was stirred for 5 hours under reflux. To the reaction solution were added 10 ml of 6N hydrochloric acid saturated solution of ferric chloride and the solution was stirred at room temperature for one hour. After completion of the agitation, the reaction solution was extracted with toluene, the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentratred under reduced pressure. The resulting brown, oily product was isolated and purified by a silica gel column chromatography to afford a colourless oily substance which was recrystallized from ethanol to afford colourless crystal. This was identified as the title compound by analytical results.

Workup

  1. temperatureunder reflux
  2. stirringthe solution was stirred at room temperature for one hour
  3. extractionAfter completion of the agitation, the reaction solution was extracted with toluene
  4. washthe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe resulting brown, oily product was isolated
  7. custompurified by a silica gel column chromatography
  8. customto afford a colourless oily substance which
  9. customwas recrystallized from ethanol
  10. customto afford colourless crystal

Sources & evidence

ORD record
ord-7208f065d3fb47568cda05c9a36c664f
Source dataset
uspto-grants-2000_01
Patent number
US06017467

Reaction notes

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