Sodium Cyanide → 5-(2-Propyl-3,4-dichlorophenoxy)pentane nitrile

HRID 34970Notes

Reaction equation

HRID 34970 reaction equation
[CH2:1]([C:4]1[C:16]([Cl:17])=[C:15]([Cl:18])[CH:14]=[CH:13][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]Br)[CH2:2][CH3:3].[C-]#[N:20].[Na+]>CN(C)C=O>[CH2:1]([C:4]1[C:16]([Cl:17])=[C:15]([Cl:18])[CH:14]=[CH:13][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[N:20])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 212972695-(2-Propyl-3,4-dichlorophenoxy)pentyl bromide

Product 1

HCID 212972585-(2-Propyl-3,4-dichlorophenoxy)pentane nitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.6 g. of 5-(2-propyl-3,4dichlorophenoxy)pentyl bromide and 0.22 g. of sodium cyanide were heated overnight at 75°-85° C. in 50 ml. of dimethylformamide. The solution was evaporated in vacuo and ethyl acetate and water were added to the residue. The layers were separated and the organic layer was washed several times with a saturated sodium chloride solution. The organic solution was filtered through sodium sulfate and evaporated to dryness to give 1.38 g. of the desired sub-title intermediate. NMR.

Workup

  1. customThe solution was evaporated in vacuo and ethyl acetate and water
  2. additionwere added to the residue
  3. customThe layers were separated
  4. washthe organic layer was washed several times with a saturated sodium chloride solution
  5. filtrationThe organic solution was filtered through sodium sulfate
  6. customevaporated to dryness
  7. customto give 1.38 g

Sources & evidence

ORD record
ord-b9adf9d7b096468f83a8b7ace2b09bac
Source dataset
uspto-grants-1988_08
Patent number
US04764521

Reaction notes

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