Benzoyl Peroxide → HCID 53685615, compound

HRID 726630Notes

Reaction equation

HRID 726630 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([CH2:13][P:14]([O:18][CH3:19])([O:16][CH3:17])=[O:15])=[CH:5]2.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:38]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:38][CH2:12][C:7]1[C:6]([CH2:13][P:14]([O:16][CH3:17])([O:18][CH3:19])=[O:15])=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 54514340HCID 54514340, compound

Product 1

HCID 53685615HCID 53685615, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 6-chloro-3-(dimethylphosphonomethyl)-2-methylquinoline (0.85 g, 2.7 mmol) in carbon tetrachloride (40 ml) was treated with benzoyl peroxide (100 mg) followed by N-bromosuccinimide (0.50 g, 2.8 mmol). The reaction mixture was refluxed for 4 hours, filtered and concentrated in vacuo. The residue was flash chromatographed on silica gel with ethyl acetate as the eluent to give 0.75 g of 2-bromomethyl-6-chloro-3-(dimethylphosphonomethyl)quinoline.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customchromatographed on silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-af4a4d9a73b742ec9209d139dc93e08e
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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