Chlorosuccinimide → 3-Bromo-5-(3-chloroprop-1-en-2-yl)pyridine

HRID 1087940

Reaction equation

HRID 1087940 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([CH3:10])=[CH2:9])[CH:7]=1.[Cl:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([CH2:10][Cl:11])=[CH2:9])[CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 234368083-Bromo-5-(prop-1-en-2-yl)pyridine

Product 1

HCID 150087163-Bromo-5-(3-chloroprop-1-en-2-yl)pyridineYield 26.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7.12 g of 3-bromo-5-isopropenylpyridine, 6.85 g of N-chlorosuccinimide and 15 ml of carbon tetrachloride was stirred at 80° C. for 7 hours. After the reaction mixture was cooled to room temperature, the insoluble matter was filtered out. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (eluted with ethyl acetate-n-hexane 1:19) to obtain 2.23 g of the objective compound.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationthe insoluble matter was filtered out
  3. concentrationThe filtrate was concentrated under a reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluted with ethyl acetate-n-hexane 1:19)

Sources & evidence

ORD record
ord-16153fa341e84867969f859575033355
Source dataset
uspto-grants-1990_10
Patent number
US04960897

Linked notes

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