Benzoyl Peroxide → 3-(bromomethyl)-1-methylpyridin-2(1H)-one

HRID 706697Notes

Reaction equation

HRID 706697 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]1=[O:9].[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:10][CH2:8][C:4]1[C:3](=[O:9])[N:2]([CH3:1])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2854801,3-Dimethyl-2-pyridone

Product 1

HCID 122726633-(bromomethyl)-1-methylpyridin-2(1H)-oneYield 32.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1,3-Dimethylpyridin-2(1H)-one (0.54 g, 4.4 mmol) was added to CCl4 (100 mL). N-Bromosuccinimide (0.78 g, 4.4 mmol) and benzoyl peroxide (0.11 g, 0.44 mmol) were added and the reaction mixture was refluxed for 3 hours. The reaction was cooled, filtered and concentrated. The residue was suspended in Et2O (10 mL) and filtered to provide 3-(bromomethyl)-1-methylpyridin-2(1H)-one (0.29 g, 32% yield) as a solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. concentrationconcentrated
  5. filtrationfiltered

Sources & evidence

ORD record
ord-f054741b23294e8294bdd4aec458ed22
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

Loading…