Benzoyl Peroxide → 2-(Bromomethyl)quinoxaline

HRID 577220Notes

Reaction equation

HRID 577220 reaction equation
[CH3:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Br:12]N1C(=O)CCC1=O.C1(C(OOC(=O)C2C=CC=CC=2)=O)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 236862-MethylquinoxalineHCID 67184N-bromobutanimide

Product 1

HCID 52877592-(Bromomethyl)quinoxalineYield 46.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-methylquinoxaline (1 g, 6.9 mmol) was dissolved in CCl4 (15 mL), and then 1-bromopyrrolidine-2,5-dione (1.8 g, 10.4 mmol) and benzoyl benzenecarboperoxoate (1.0 g, 4.2 mmol) were added. The mixture was stirred overnight at reflux. The solids were removed by filtration. The filtrate was washed with brine and dried over sodium sulfate. After evaporation of the solvent, the residue was dissolved in DCM and purified on silica gel using 40% hexane/AcOEt to afford 2-(bromomethyl)quinoxaline (714 mg, 46% yield); 1H NMR (400 MHz, DMSO-d6): δ 4.94 (s, 2H), 7.84-7.90 (m, 2H), 8.04-8.11 (m, 2H), 9.09 (s, 1H).

Workup

  1. temperatureat reflux
  2. customThe solids were removed by filtration
  3. washThe filtrate was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvent
  6. dissolutionthe residue was dissolved in DCM
  7. custompurified on silica gel using 40% hexane/AcOEt

Sources & evidence

ORD record
ord-6061d827574d475083aaa253e02631dc
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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