Potassium Cyanide → 3-Chloro-2-iodobenzeneacetonitrile

HRID 2078352Notes

Reaction equation

HRID 2078352 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-c0c40784a4724e1cac3af34928208174
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

Loading…