Potassium Cyanide → 3-Chloro-2-iodobenzeneacetonitrile

HRID 1868944Notes

Reaction equation

HRID 1868944 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[I:10].[C-:11]#[N:12].[K+]>CCO.O>[Cl:9][C:5]1[C:4]([I:10])=[C:3]([CH2:2][C:11]#[N:12])[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 670998331035263-40-1

Product 1

HCID 670996963-Chloro-2-iodobenzeneacetonitrileYield 54.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-(bromomethyl)-3-chloro-2-iodobenzene (7 g, 21 mmol) in 100 mL EtOH was treated with a solution of potassium cyanide (2 mL, 42 mmol) in 20 mL water. The mixture was refluxed for 2.5 hours. The mixture was cooled to room temperature and concentrated. The residue was diluted with 200 mL EtOAc, washed with water (2×50 mL), saturated NaCl (50 mL), dried over anhydrous sodium sulfate and concentrated. The crude product was purified by column chromatography (20% EtOAc/hexane) to give 3.2 g pale yellow solid. MS m/e: (M+H)+ 278.

Workup

  1. temperatureThe mixture was refluxed for 2.5 hours
  2. concentrationconcentrated
  3. additionThe residue was diluted with 200 mL EtOAc
  4. washwashed with water (2×50 mL), saturated NaCl (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-d8e7260cdeb048db8aec7358a53e8f26
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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