Sodium Iodide → 4-Chloro-2-[[(1r)-4-iodo-1-phenylbutyl]oxy]benzonitrile

HRID 352104Notes

Reaction equation

HRID 352104 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14]Cl)[CH:3]=1.[I-:22].[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14][I:22])[CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 698293454-Chloro-2-[[(1r)-4-chloro-1-phenylbutyl]oxy]benzonitrile

Product 1

HCID 698282664-Chloro-2-[[(1r)-4-iodo-1-phenylbutyl]oxy]benzonitrileYield 89.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of the product from step (b) (2.80 g) and sodium iodide (20 g) in acetone (100 ml) was heated under reflux for 20 h. The mixture was filtered, evaporated, dissolved in water (50 ml) and extracted with ethyl acetate (three times). The organic extracts were washed with water, dried (magnesium sulphate) and evaporated to give the title compound (3.22 g).

Workup

  1. temperatureunder reflux for 20 h
  2. filtrationThe mixture was filtered
  3. customevaporated
  4. dissolutiondissolved in water (50 ml)
  5. extractionextracted with ethyl acetate (three times)
  6. washThe organic extracts were washed with water
  7. dry with materialdried (magnesium sulphate)
  8. customevaporated

Sources & evidence

ORD record
ord-7a27ffd422234668b1774412e87fb8de
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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