Benzoyl Peroxide → 2-(Bromomethyl)-3-phenylquinoxaline

HRID 1948718Notes

Reaction equation

HRID 1948718 reaction equation
[CH3:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C1C(=O)N([Br:25])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:25][CH2:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[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 67184N-bromobutanimideHCID 3469032-Methyl-3-phenylquinoxaline

Product 1

HCID 144745412-(Bromomethyl)-3-phenylquinoxalineYield 49.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-methyl-3-phenylquinoxaline (2.00 g, 9.08 mmol), NBS (1.45 g, 8.17 mmol) and benzoyl peroxide (catalytic amount) in carbon tetrachloride (75 mL) was heated at reflux for 5 h, then allowed to cool to r.t. The reaction mixture was filtered, the filtrate was concentrated in vacuo and the residue purified by column chromatography (SiO2, 0-20% EtOAc in heptane) to give the title compound (1.22 g, 45%) as a cream-coloured solid. δH (CDCl3) 8.11-8.19 (m, 2H), 7.75-7.85 (m, 4H), 7.52-7.62 (m, 3H), 4.76 (s, 2H). LCMS (ES+) 299.1, 301.1 (M+H)+, RT 4.10 minutes (Method 3).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue purified by column chromatography (SiO2, 0-20% EtOAc in heptane)

Sources & evidence

ORD record
ord-0169b5baa20c43108b10ddb9eee75f9f
Source dataset
uspto-grants-2013_03
Patent number
US08399483B2

Reaction notes

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