Benzene → 2-Chloro-6-(3-chloroprop-1-en-2-yl)pyridine

HRID 1087936Notes

Reaction equation

HRID 1087936 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH3:10])=[CH2:9])[N:3]=1.[Cl:11]N1C(=O)CCC1=O.C1C=CC=CC=1>CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH2:10][Cl:11])=[CH2:9])[N:3]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 31398ChlorosuccinimideHCID 150087102-Chloro-6-isopropenylpyridine

Product 1

HCID 150087112-Chloro-6-(3-chloroprop-1-en-2-yl)pyridineYield 56.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 29.8 g of 2-chloro-6-isopropenylpyridine, 29.8 g of N-chlorosuccinimide and 60 ml of benzene was stirred at 80° C. for 5 hours. After the reaction mixture was cooled to room temperature, 200 ml of n-hexane was added thereto to remove the insoluble matter through filtration. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluted with n-hexane then n-hexane - ethyl acetate 20:1) to obtain 20.6 g of the objective compound.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customto remove the insoluble matter
  3. filtrationthrough filtration
  4. distillationAfter distilling off the solvent
  5. customthe residue was purified by silica gel column chromatography (
  6. washeluted with n-hexane

Sources & evidence

ORD record
ord-733349a189ae46eeafa73408a7d4f3cc
Source dataset
uspto-grants-1990_10
Patent number
US04960897

Reaction notes

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