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

HRID 1087939Notes

Reaction equation

HRID 1087939 reaction equation
[Br: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>[Br: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 221642832-Bromo-6-(prop-1-en-2-yl)pyridine

Product 1

HCID 150087152-Bromo-6-(3-chloroprop-1-en-2-yl)pyridineYield 35.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3.60 g of 2-bromo-6-isopropenylpyridine, 2.91 g of N-chlorosuccinimide and 8 ml of benzene was stirred at 80° C. for 5 hours. After the reaction mixture was cooled to room temperature, 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 1.50 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-b7d5909c2c024bb2ae7265eead7b8df9
Source dataset
uspto-grants-1990_10
Patent number
US04960897

Reaction notes

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