Benzoyl Peroxide → 5-(Bromomethyl)pyridine-2-carbonitrile

HRID 1835673Notes

Reaction equation

HRID 1835673 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1)#[N:2].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:28]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([C:3]1[N:8]=[CH:7][C:6]([CH2:9][Br:28])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 741835-Methylpicolinonitrile

Product 1

HCID 219277275-(Bromomethyl)pyridine-2-carbonitrileYield 51%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 6-cyano-3-picoline (1.32 g, 11.19 mmol), benzoylperoxide (0.54 g, 2.24 mmol), and N-bromosuccinimide (2.8 g, 15.7 mmol) in carbontetrachloride (30 mL) was heated at reflux for 2 h. The resulting suspension was filtered and the filtrate diluted with dichloromethane (400 mL), washed with a saturated sodium bicarbonate solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (EtOAc:n-hexane, 1:9) to give the title compound as a yellow oil (1.12 g, 51%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. filtrationThe resulting suspension was filtered
  4. additionthe filtrate diluted with dichloromethane (400 mL)
  5. washwashed with a saturated sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (EtOAc:n-hexane, 1:9)

Sources & evidence

ORD record
ord-5e7a8ffb01e54ae6bd2f1ebcf99a6c02
Source dataset
uspto-grants-2004_08
Patent number
US06774110B2

Reaction notes

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