Azobisisobutyronitrile → 2-(Bromomethyl)-3-methoxypyrazine

HRID 604689Notes

Reaction equation

HRID 604689 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[N:7][CH:6]=[CH:5][N:4]=1.[Br:10]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:10][CH2:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 178982-Methoxy-3-methylpyrazineHCID 67184N-bromobutanimide

Product 1

HCID 533855142-(Bromomethyl)-3-methoxypyrazine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-methoxy-3-methylpyrazine (0.943 mL, 8.06 mmol), N-bromosuccinimide (1.505 g, 8.46 mmol) and 2,2′-azobis(2-methylpropionitrile) (0.132 g, 0.806 mmol) were heated at reflux in CCl4 (65.5 mL) (oil bath=100° C.) for 2.5 h. LCMS indicated formation of the product. The crude mixture was cooled, filtered and purified by flash chromatography (SiO2, Biotage 40M cartridge). The column was eluted with a CH2Cl2/hexanes mixture (0% to 100%). Related fractions were pooled and co-evaporated with toluene to afford a toluene solution (30 mL) of the product. To be used as it was for next step.

Workup

  1. filtrationfiltered
  2. custompurified by flash chromatography (SiO2, Biotage 40M cartridge)
  3. washThe column was eluted with a CH2Cl2/hexanes mixture (0% to 100%)
  4. customto afford a toluene solution (30 mL) of the product

Sources & evidence

ORD record
ord-cc4bdc91bf4e4d0180d48429267a3700
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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