Benzoyl Peroxide → Methyl 4-(bromomethyl)-6-chloronicotinate

HRID 339987Notes

Reaction equation

HRID 339987 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:10]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=[C:2]([Cl:1])[CH:11]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 46223836Methyl 6-chloro-4-methylpyridine-3-carboxylate

Product 1

HCID 86681474Methyl 4-(bromomethyl)-6-chloronicotinate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 6-chloro-4-methylnicotinate (2.50 g, 13.5 mmol), N-bromosuccinimide (2.88 g, 16.2 mmol) and benzoyl peroxide (0.14 g, 0.56 mmol) in carbon tetrachloride (100 mL) was refluxed under an atmosphere of nitrogen overnight. The mixture was cooled to room temperature, and filtered through a pad of celite. The mixture was concentrated. The residue was purified by combi-flash chromatography (ethyl acetate in hexanes: 30%) to afford the desired product.

Workup

  1. temperaturewas refluxed under an atmosphere of nitrogen overnight
  2. filtrationfiltered through a pad of celite
  3. concentrationThe mixture was concentrated
  4. customThe residue was purified by combi-flash chromatography (ethyl acetate in hexanes: 30%)

Sources & evidence

ORD record
ord-75aeff83ff1645f8a7edc269fd1c37b4
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

Loading…