Dichloromethane → 6-(Bromomethyl)quinoxaline

HRID 577000Notes

Reaction equation

HRID 577000 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.ClCCl>C(Cl)(Cl)(Cl)Cl>[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 4

HCID 6344DichloromethaneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2425676-Methylquinoxaline

Product 1

HCID 102145106-(Bromomethyl)quinoxalineYield 35.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 6-methylquinoxaline (2.0 g, 13.9 mmol), N-bromosuccinimide (3.0 g, 16.9 mmol), and benzoyl peroxide (411 mg, 1.7 mmol) in anhydrous carbon tetrachloride (50 mL) was stirred at reflux for 2 days. Dichloromethane (50 mL) was added after cooling to room temperature. The mixture was extracted with 1 N NaOH (1×100 mL) and brine (1×100 mL). The organic extract was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-30% EtOAc/hexanes), affording 6-(bromomethyl)quinoxaline (1.10 g, 35% yield).

Workup

  1. temperatureat reflux for 2 days
  2. extractionThe mixture was extracted with 1 N NaOH (1×100 mL) and brine (1×100 mL)
  3. extractionThe organic extract
  4. customwas recovered
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customdried in vacuo
  9. customThe crude product was purified by flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-75f209f143714b4394b116a324d33ac7
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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