Potassium Cyanide → 2-Chloro-6-iodobenzeneacetonitrile

HRID 1868933Notes

Reaction equation

HRID 1868933 reaction equation
Br[CH2:2][C:3]1[C:8]([I:9])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:10].[C-:11]#[N:12].[K+]>CCO.O>[Cl:10][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([I:9])[C:3]=1[CH2:2][C:11]#[N:12]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 670999852-(Bromomethyl)-1-chloro-3-iodobenzene

Product 1

HCID 670998812-Chloro-6-iodobenzeneacetonitrileYield 87.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-(bromomethyl)-1-chloro-3-iodobenzene (14 g, 42 mmol) in 100 mL EtOH was treated with a solution of potassium cyanide (3.6 mL, 84 mmol) in 40 mL water. The mixture was refluxed for 2.5 hours. The mixture was cooled to room temperature and then concentrated. The residue was diluted with 200 mL EtOAc, washed with water (2×50 mL), saturated NaCl (50 mL), dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (20% EtOAc/hexane) to give 10.18 g pale yellow solid. MS m/e: (M−1)− 276.

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 sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-e0c0c105c71d46798e1d2f984181ef32
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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