Benzoyl Peroxide → 2-(Bromomethyl)-3,5,6-trimethylpyrazine

HRID 877910Notes

Reaction equation

HRID 877910 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[N:4][C:3]=1[CH3:10].C1C(=O)N([Br:18])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:10][C:3]1[C:2]([CH3:1])=[N:7][C:6]([CH3:8])=[C:5]([CH3:9])[N:4]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 14296Tetramethylpyrazine3×HCID 67184N-bromobutanimide2×

Product 1

HCID 135849922-(Bromomethyl)-3,5,6-trimethylpyrazine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

More preferably, dissolving dehydrated tetramethylpyrazine into an organic solvent, preferably CCl4, and adding NBS at a molar ratio of tetramethylpyrazine to NBS=1:0.7, adding a small amount of benzoylperoxide as the radical initiator, reacting with the illumination of an incandescent lamp and reacting for 10-12 h under reflux, then cooling and condensing the reaction liquid, and sucking away the excess tetramethylpyrazine under reduced pressure in 60-70° C. water bath, the residue being kept in a fridge for standing and thus 2-bromomethyl-3,5,6-trimethylpyrazine being obtained as a pale-red half-oily substance.

Workup

  1. customreacting with the illumination of an incandescent lamp
  2. temperatureunder reflux
  3. temperaturecooling
  4. customcondensing
  5. customthe reaction liquid
  6. customin 60-70° C.

Sources & evidence

ORD record
ord-fb0fb0c014ed41ceb3065a5f4eb49124
Source dataset
uspto-grants-2015_03
Patent number
US08987449B2

Reaction notes

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