Sodium Iodide → 4-Chloro-5-fluoro-2-{[(1R)-3-iodo-1-phenylpropyl]oxy}benzonitrile

HRID 2179948Notes

Reaction equation

HRID 2179948 reaction equation
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:11][C@@H:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13][CH2:14]Cl)[CH:3]=1.[I-:22].[Na+]>CC(C)=O>[Cl:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:11][C@@H:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13][CH2:14][I:22])[CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 697982114-Chloro-2-{[(1R)-3-chloro-1-phenylpropyl]oxy}-5-fluorobenzonitrile

Product 1

HCID 697986504-Chloro-5-fluoro-2-{[(1R)-3-iodo-1-phenylpropyl]oxy}benzonitrileYield 98.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Chloro-2-{[(1R)-3-chloro-1-phenylpropyl]oxy}-5-fluorobenzonitrile (1.8 , 5.6 mmol) and sodium iodide (12.8 g, 100 mmol) were dissolved in acetone (50 ml) and heated under reflux for 24 h. The reaction mixture was cooled, filtered and evaporated. The semi-solid residue was dissolved in toluene, filtered and evaporated again to give 2.3 g of the crude product as a yellow oil. This was used without purification for the next step.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe semi-solid residue was dissolved in toluene
  7. filtrationfiltered
  8. customevaporated again

Sources & evidence

ORD record
ord-46f53ecfc628469288051ea108db9558
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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