Benzoyl Peroxide → 3-Bromo-5-(bromomethyl)-2-chloropyridine

HRID 633592Notes

Reaction equation

HRID 633592 reaction equation
[Br:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[Br:10]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[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([CH2:8][Br:10])[CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2854373-Bromo-2-chloro-5-methylpyridine

Product 1

HCID 848198723-Bromo-5-(bromomethyl)-2-chloropyridineYield 34.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-Bromo-2-chloro-5-methylpyridine (4 g, 19.37 mmol), N-bromosuccinimide (3.79 g, 21.3 mmol) and benzoic peroxyanhydride (0.239 g, 0.969 mmol) were combined in carbon tetrachloride (40 mL), heated under reflux for 24 hours, cooled, and filtered to remove succinimide. The filtrate was concentrated. The resulting residue was purified by chromatography (silica gel, 0-30% ethyl acetate in heptanes) to afford the title compound (1.9 g, 34%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customto remove succinimide
  6. concentrationThe filtrate was concentrated
  7. customThe resulting residue was purified by chromatography (silica gel, 0-30% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-5f1e9721a6ad4763840e47cbb6a5ba51
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

Loading…