Sodium Iodide → Benzonitrile, 4-[(5-iodopentyl)oxy]-

HRID 732246

Reaction equation

HRID 732246 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.CC(=O)CC.[I-:21].[Na+]>C(OC(=O)C)C>[I:21][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6569Methyl Ethyl KetoneHCID 193815104-((5-Chloropentyl)oxy)benzonitrile

Product 1

HCID 16202445Benzonitrile, 4-[(5-iodopentyl)oxy]-Yield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

While 50 g of 4-(5-chloro-pentoxy)-benzonitrile (8) prepared in Example 5 were added to 500 ml of 2-butanone and stirred, 167 g of sodium iodide were added. Subsequently, the reaction temperature was gradually increased and stirring was continued at 70-80° C. for 6 hr. After the reaction was completed, the reaction temperature was decreased to room temperature, and the resultant reaction mixture was added with 1 L of ethylacetate, and then washed with water and brine. The ethylacetate layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residual solution was crystallized with methylalcohol, thus obtaining 69.7 g (yield: 99%) of a title compound as a white solid.

Workup

  1. temperatureSubsequently, the reaction temperature was gradually increased
  2. stirringstirring
  3. customwas decreased to room temperature
  4. customthe resultant reaction mixture
  5. washwashed with water and brine
  6. dry with materialThe ethylacetate layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residual solution was crystallized with methylalcohol

Sources & evidence

ORD record
ord-e4f7c9701fa94bc2b4963889c6315dde
Source dataset
uspto-grants-2009_09
Patent number
US07585979B2

Linked notes

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