Benzoyl Peroxide → 6-(Bromomethyl)quinoxaline

HRID 1008810Notes

Reaction equation

HRID 1008810 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.C1C(=O)N([Br:19])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:19][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

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2425676-Methylquinoxaline

Product 1

HCID 102145106-(Bromomethyl)quinoxalineYield 77.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 6-methylquinoxaline (10.0 g, 69.4 mmol) in CCl4 (80 mL) was added NBS (13.5 g, 76.3 mmol) and benzoyl peroxide (BP, 1.7 g, 6.9 mmol) at room temperature. The mixture was heated at reflux for 2 hours. After cooling, the mixture was evaporated under vacuum to give a yellow solid, which was extracted with Petroleum Ether (50 mL×5). The extracts were concentrated under vacuum. The organics were combined and concentrated to give crude 6-bromomethylquinoxaline (12.0 g), which was used directly in the next step. 1H NMR (300 MHz, CDCl3) δ 8.85-8.87 (m, 2 H), 8.10-8.13 (m, 2 H), 7.82 (dd, J=2.1, 8.7 Hz, 1 H), 4.70 (s, 2 H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling
  4. customthe mixture was evaporated under vacuum
  5. customto give a yellow solid, which
  6. extractionwas extracted with Petroleum Ether (50 mL×5)
  7. concentrationThe extracts were concentrated under vacuum
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ac11a721c2cb4b4584f5fcbb01e02af9
Source dataset
uspto-grants-2011_07
Patent number
US07973038B2

Reaction notes

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