Benzoyl Peroxide → (7-Bromo-quinolin-2-yl)methylbromide

HRID 1088467Notes

Reaction equation

HRID 1088467 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][Br:13])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 123328967-Bromo-2-methylquinoline

Product 1

HCID 22163097(7-Bromo-quinolin-2-yl)methylbromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 220 g 7-bromoquinaldine, 180 g N-bromosuccinimide and 1 g dibenzoylperoxide in CCl4 (1 L) was illuminated with a 275 W sun lamp at reflux for 12 hours. The reaction mixture was cooled and directly chromatographed on 2 kg silica gel. Elution with toluene afforded the title compound which was used as is for the next step.

Workup

  1. customwas illuminated with a 275 W sun lamp
  2. temperatureat reflux for 12 hours
  3. temperatureThe reaction mixture was cooled
  4. customdirectly chromatographed on 2 kg silica gel
  5. washElution with toluene

Sources & evidence

ORD record
ord-ca978d4c001a4ffc80af50722d6f7f92
Source dataset
uspto-grants-1990_10
Patent number
US04962203

Reaction notes

Loading…