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

HRID 877911Notes

Reaction equation

HRID 877911 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-trimethylpyrazineYield 70%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Dehydrated tetramethylpyrazine 10 g was dissolved into CCl4 60 ml and then NBS 9.17 g was added at a molar ratio of tetramethylpyrazine to NBS=1:0.7 (a minute amount of benzoylperoxide can be added as radical initiator). Reaction was carried out under reflux under the illumination of an incandescent lamp for 10-12 h. The reaction sample was cooled and condensed, and the excess tetramethylpyrazine was sucked away at reduced pressure in 60-70° C. water bath. The residue was kept in a fridge for standing and a pale red half-oily substance 7.75 g was obtained with a yield of 70%.

Workup

  1. additioncan be added as radical initiator)
  2. customReaction
  3. temperatureunder reflux under the illumination of an incandescent lamp for 10-12 h
  4. temperatureThe reaction sample was cooled
  5. customcondensed
  6. customwas sucked away at reduced pressure in 60-70° C.
  7. customa pale red half-oily substance 7.75 g was obtained with a yield of 70%

Sources & evidence

ORD record
ord-1827b683282145c18d021db13c323e43
Source dataset
uspto-grants-2015_03
Patent number
US08987449B2

Reaction notes

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