Acetone → 2-Chloro-6-(l-iodomethylvinyl)pyridine

HRID 1087938Notes

Reaction equation

HRID 1087938 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH2:10]Cl)=[CH2:9])[N:3]=1.[I-:12].[K+].CC(C)=O.CN(C)C=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH2:10][I:12])=[CH2:9])[N:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 4875Potassium IodideHCID 6228DimethylformamideHCID 150087112-Chloro-6-(3-chloroprop-1-en-2-yl)pyridine

Product 1

HCID 150087142-Chloro-6-(l-iodomethylvinyl)pyridineYield 60.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.50 g of 2-chloro-6-(1-chloromethylvinyl) pyridine, 0.88 g of potassium iodide, 5 ml of acetone and 0.5 ml of N,N-dimethylformamide was stirred at 50° to 60° C. for 5 hours. After the reaction mixture was cooled to room temperature, water was added thereto to extract the mixture with ethyl acetate. The extract was subsequently washed with an aqueous solution of 10% sodium thiosulfate, water, saturated saline solution in that order, and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluted with dichloromethane) to obtain 0.45 g of the objective compound.

Workup

  1. extractionto extract the mixture with ethyl acetate
  2. washThe extract was subsequently washed with an aqueous solution of 10% sodium thiosulfate, water, saturated saline solution in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent
  5. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane)

Sources & evidence

ORD record
ord-f359e0db42334c3cb960a771f72f3bea
Source dataset
uspto-grants-1990_10
Patent number
US04960897

Reaction notes

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