Chlorosuccinimide → 2-(4-(Chloromethyl)phenyl)pyridine

HRID 7379Notes

Reaction equation

HRID 7379 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:3][CH:2]=1.[Cl:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:4]1[CH:5]=[CH:6][C:1]([CH2:13][Cl:14])=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 782192-(p-Tolyl)pyridine

Product 1

HCID 219897292-(4-(Chloromethyl)phenyl)pyridineYield 53.8%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-(p-tolyl)pyridine (1.7 g) and N-chlorosuccinimide (1.5 g) in carbon tetrachloride (30 mL) was added α,α-azobisisobutyronitrile (0.033 g), and the mixture was heated under reflux for 5 hours. Insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1-3/1) to give 4-(pyridin-2-yl)benzyl chloride (1.1 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customInsoluble materials were removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1-3/1)

Sources & evidence

ORD record
ord-6744837d271542169edc181f1b3dfcd3
Source dataset
uspto-grants-2006_08
Patent number
US07087579B2

Reaction notes

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