Benzoyl Peroxide → 2-Bromo-5-bromomethylpyridine

HRID 365466Notes

Reaction equation

HRID 365466 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Br:9]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 64246602-Bromo-5-bromomethylpyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a flask was charged 2-bromo-5-methylpyridine (34.9 mmol, 6.0 g), N-bromosuccinimide (38.4 mmol, 6.83 g), benzoyl peroxide (3.49 mmol, 0.85 g) and carbon tetrachloride (60 mL). This solution was refluxed for 6 hr, cooled to ambient temperature and purified on a silica gel column. Eluted with ethyl acetate: hexane (1:9) to provide the title compound. FAB MS: calc: 250.9 found: 251.9. 1H-NMR (CDCl3): 4.4 ppm (s, 2H); 7.5 ppm (d, 1H); 7.6 ppm (d, 1H); 8.4 ppm (s, 1H).

Workup

  1. temperatureThis solution was refluxed for 6 hr
  2. custompurified on a silica gel column
  3. washEluted with ethyl acetate: hexane (1:9)

Sources & evidence

ORD record
ord-cba6d2f764a641fc9a6b9f3c80875b00
Source dataset
uspto-grants-2000_10
Patent number
US06127390

Reaction notes

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