Benzoyl Peroxide → 6-(Bromomethyl)quinoxaline

HRID 729495Notes

Reaction equation

HRID 729495 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[N:5]2.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1.C(OCC)(=O)C>[Br:12][CH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[N:5]2

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2425676-Methylquinoxaline

Product 1

HCID 102145106-(Bromomethyl)quinoxaline

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-methylquinoxaline (1.5 g, 10.4 mmol), N-bromosuccinimide (2.2 g, 12.5 mmol) and benzoylperoxide (0.30 g, 1.25 mmol) in benzene (35 mL) was stirred rapidly and heated to reflux for 5 h. Upon cooling, the mixture was diluted with ethyl acetate (25 mL), washed with IN sodium hydroxide solution (50 mL) and saturated sodium chloride solution (50 mL). The organic layer was dried (MgSO4) and evaporated to a crystalline solid (2.5 g, 77% desired product, 23% α,α-dibrominated product as determined by 1H NMR). The mixture was used in subsequent reactions.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 h
  3. temperatureUpon cooling
  4. washwashed with IN sodium hydroxide solution (50 mL) and saturated sodium chloride solution (50 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated to a crystalline solid (2.5 g, 77% desired product, 23% α,α-dibrominated product as determined by 1H NMR)

Sources & evidence

ORD record
ord-010b38584b654ac6884ec375e6ffe669
Source dataset
uspto-grants-2009_09
Patent number
US07582636B2

Reaction notes

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