Benzoyl Peroxide → HCID 86686337, compound

HRID 1043904Notes

Reaction equation

HRID 1043904 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[N:4][C:5]([CH3:9])=[CH:6][C:7]=1[CH3:8].C1C(=O)N([Br:18])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([CH2:10][Br:18])=[N:4][C:5]([CH3:9])=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 251368433-Bromo-2,4,6-trimethylpyridine

Product 1

HCID 86686337HCID 86686337, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-bromo-2,4,6-trimethylpyridine (15.6 g), NBS (13.9 g) and benzoyl peroxide (567 mg) was heated under reflux in a carbon tetrachloride solvent (300 mL) for two hours. The reaction mixture was cooled to room temperature and then filtered, and the filtration residue was washed with carbon tetrachloride. The resulting filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 10%) to give the title compound (3.51 g).

Workup

  1. temperaturewas heated
  2. filtrationfiltered
  3. washthe filtration residue was washed with carbon tetrachloride
  4. concentrationThe resulting filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 10%)

Sources & evidence

ORD record
ord-2f60003e39714ad08b85ed9ead46deec
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

Loading…