Potassium Cyanide → 3-Bromo-6-(phenylthio)-phenylacetonitrile

HRID 435694Notes

Reaction equation

HRID 435694 reaction equation
[C-:1]#[N:2].[K+].[Br:4][C:5]1[CH:6]=[C:7]([C:10]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)[CH2:8]Cl>O>[Br:4][C:5]1[CH:6]=[C:7]([CH2:8][C:1]#[N:2])[C:10]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 214560373-Bromo-6-(phenylthio)-benzyl chloride

Product 1

HCID 214811343-Bromo-6-(phenylthio)-phenylacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

136.5 g of potassium cyanide in 183 ml of water are heated under reflux for 10 hours under a nitrogen atmosphere with 470 g of 3-bromo-6-(phenylthio)-benzyl chloride. The ethanol is distilled off under reduced pressure, the residue diluted with water and extracted with ether. The extracts are washed with water, dried over magnesium sulphate and evaporated. There is obtained 3-bromo-6-(phenylthio)-phenylacetonitrile as a brown oil.

Workup

  1. distillationThe ethanol is distilled off under reduced pressure
  2. additionthe residue diluted with water
  3. extractionextracted with ether
  4. washThe extracts are washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-663544e8b1624638ab6c5cbb787c4e51
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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