N-bromobutanimide → 3-Bromo-2-(bromomethyl)pyridine

HRID 2380865Notes

Reaction equation

HRID 2380865 reaction equation
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([CH2:8][Br:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12010033-Bromo-2-methylpyridine

Product 1

HCID 214410813-Bromo-2-(bromomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-Bromo-2-methylpyridine (10.0 g, 58.1 mmol), diphenylperoxyanhydride (2.82 g, 11.6 mmol), 1-bromopyrrolidine-2,5-dione (10.9 g, 61.0 mmol) were refluxed in 233 mL of carbon tetrachloride for 144 hours. The reaction mixture was cooled to ambient temperature and washed with water (3×200 mL). The organic layer was dried over Na2SO4, filtered, concentrated, and purified by silica gel chromatography eluting with 0-30% EtOAc in hexanes to provide 3-bromo-2-(bromomethyl)pyridine.

Workup

  1. washwashed with water (3×200 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography
  6. washeluting with 0-30% EtOAc in hexanes

Sources & evidence

ORD record
ord-e580d168dd944caabc0c952fc585fcb2
Source dataset
uspto-grants-2012_09
Patent number
US08258135B2

Reaction notes

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