Benzoyl Peroxide → Methyl 6-(bromomethyl)pyridine-2-carboxylate

HRID 1777587Notes

Reaction equation

HRID 1777587 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=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[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 73022Methyl 6-methylpyridine-2-carboxylate

Product 1

HCID 21471714Methyl 6-(bromomethyl)pyridine-2-carboxylateYield 28.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 6-methylpicolinate (1.81 g; 11.97 mmol) and carbon tetrachloride (60 mL) was treated with N-bromosuccinimide (2.37 g, 13.17 mmol) and benzoyl peroxide (0.299 g; 1.20 mmol) and heated at refluxing temperature for 21 hours. The resulting brown suspension was concentrated under reduced pressure and the residue purified by flash chromatography on silica gel (eluent 0 to 6% ethyl acetate in dichloromethane) to give 0.773 g (28%) of methyl 6-(bromomethyl)picolinate as a white solid.

Workup

  1. temperatureheated
  2. temperatureat refluxing temperature for 21 hours
  3. concentrationThe resulting brown suspension was concentrated under reduced pressure
  4. customthe residue purified by flash chromatography on silica gel (eluent 0 to 6% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-7111f2b715d4405db83eb35313dadef3
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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