Benzoyl Peroxide → 6-(Bromomethyl)quinoxaline

HRID 491417Notes

Reaction equation

HRID 491417 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 1N 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 the mixture
  4. washwashed with 1N 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-6dbd6e00b16d4c228339be63447f929b
Source dataset
uspto-grants-2009_05
Patent number
US07531542B2

Reaction notes

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