Benzoyl Peroxide → Methyl 4-(bromomethyl)-6-chloronicotinate
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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.