Benzoyl Peroxide → Methyl 5-(bromomethyl)pyridine-2-carboxylate

HRID 1777538Notes

Reaction equation

HRID 1777538 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 268759Methyl 5-methylpicolinate

Product 1

HCID 19699469Methyl 5-(bromomethyl)pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of methyl 5-methylpicolinate (1.25 g; 8.27 mmol) in carbon tetrachloride (45 mL) was added N-bromosuccinimide (1.78 g, 9.92 mmol) and benzoyl peroxide (0.205 g; 0.827 mmol). The mixture was refluxed for 18 hours and the resulting suspension was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent 0 to 8% ethyl acetate in dichloromethane) to 0.450 g (24%) of methyl 5-(bromomethyl)picolinate as a beige solid.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. concentrationthe resulting suspension was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel (eluent 0 to 8% ethyl acetate in dichloromethane) to 0.450 g (24%) of methyl 5-(bromomethyl)picolinate as a beige solid

Sources & evidence

ORD record
ord-39f8b697f6ad48588debfcbbfb163201
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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