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

HRID 2373851

Reaction equation

HRID 2373851 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([CH3:11])=[CH:7][N:6]=1)=[O:4].C1C(=O)N([Br:19])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([CH2:11][Br:19])=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 4650652-Pyrazinecarboxylic acid, 5-methyl-, methyl ester

Product 1

HCID 21973569Methyl 5-(bromomethyl)pyrazine-2-carboxylateYield 29.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5-methyl-pyrazine-2-carboxylic acid methyl ester (2.0 g, 13.146 mmol) in CCl4 (25 mL0 was added NBS (2.57 g, 14.461 mmol) and benzoyl peroxide (0.318 g, 1.314 mmol) and the solution was heated at 70 C. for 1 h. Upon cooling to RT, the organic layer was washed with NaHCO3, water, dried (Na2SO4), and concentrated under reduced pressure to give 0.900 g 5-Bromomethyl-pyrazine-2-carboxylic acid methyl ester.

Workup

  1. temperaturethe solution was heated at 70 C
  2. washthe organic layer was washed with NaHCO3, water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-943813d9e5094dcda8d8d0ea79ce405a
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Linked notes

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