Benzoyl Peroxide → HCID 53755250, compound

HRID 726626Notes

Reaction equation

HRID 726626 reaction equation
[CH3:1][O:2][P:3]([CH2:7][C:8]1[C:9]([CH3:18])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)([O:5][CH3:6])=[O:4].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:37]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:37][CH2:18][C:9]1[C:8]([CH2:7][P:3]([O:5][CH3:6])([O:2][CH3:1])=[O:4])=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 53679805HCID 53679805, compound

Product 1

HCID 53755250HCID 53755250, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of the obtained 3-(dimethylphosphonomethyl)-2-methylquinoline (0.28 g, 1.0 mmol) in carbon tetrachloride (20 ml) was treated with benzoylperoxide (50 mg) followed by N-bromosuccinimide (0.20 g, 1.1 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 0.21 g of 2-bromomethyl-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-c8f32cd4c9e74aa7b10203b5530a6f0a
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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