Benzoyl Peroxide → 2-(Bromomethyl)-7-chloroquinoline

HRID 467292Notes

Reaction equation

HRID 467292 reaction equation
[Cl: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:13][CH2:12][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 1383957-Chloro-2-methylquinoline

Product 1

HCID 102441602-(Bromomethyl)-7-chloroquinolineYield 48.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred suspension of 7-chloroquinaldine (18.0 g, 0.10 mol), N-bromosuccinimide (18.0 g, 0.10 mol), and benzoyl peroxide (1.0 g, 0.004 mol) in CCl4 (400 mL) is illuminated with a 300 W reflector bulb for 6 hours. The reaction mixture is cooled and filtered through a plug of silica using hexane:ethyl acetate (7:3). The yellow filtrate is concentrated to give a crude mixture of unreacted starting material together with the monobromo and less polar dibromo products. The crude material is purified by flash chromatography (preabsorbed on silica Merck 60 with methylene chloride and then eluted with hexane:ethyl acetate 95:5), to yield fairly pure title product as an off-white solid. (17.31 g, 48.9% yield based on recovered starting material, m.p. 111°-112° C.).

Workup

  1. customis illuminated with a 300 W reflector bulb for 6 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered through a plug of silica
  4. concentrationThe yellow filtrate is concentrated
  5. customto give a crude
  6. additionmixture
  7. customThe crude material is purified by flash chromatography (
  8. custompreabsorbed on silica Merck 60 with methylene chloride
  9. washeluted with hexane:ethyl acetate 95:5),

Sources & evidence

ORD record
ord-f850425fe1944c91847731e87ac0ff32
Source dataset
uspto-grants-1992_10
Patent number
US05159085

Reaction notes

Loading…