Benzoyl Peroxide → 5-Bromo-5,6,7,8-tetrahydroquinoxaline

HRID 450351Notes

Reaction equation

HRID 450351 reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=[CH:3][CH:2]=1.[Br:11]NC(=O)CCC(N)=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:11][CH:9]1[CH2:8][CH2:7][CH2:6][C:5]2[N:4]=[CH:3][CH:2]=[N:1][C:10]1=2

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 368225,6,7,8-Tetrahydroquinoxaline2×HCID 9834204N-Bromosuccinamide

Product 1

HCID 177500155-Bromo-5,6,7,8-tetrahydroquinoxaline

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5,6,7,8-tetrahydroquinoxaline (Intermediate 19) (3.08 g, 23.0 mmol, commercially available) in CCl4 (200 mL) was added N-bromosuccinamide (4.09 g, 23.0 mmol) and a catalytic amount (56 mg) of benzoyl peroxide. The reaction mixture was heated at reflux for 17 hours. The reaction mixture was cooled to room temperature and filtered through Celite and concentrated in vacuo gave 5-bromo-5,6,7,8-tetrahydroquinoxaline, (Intermediate 20) (3.8 g, crude).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 17 hours
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2065a87253b74769958e58ee16057760
Source dataset
uspto-grants-2013_07
Patent number
US08486969B2

Reaction notes

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