Trimethyl phosphite → HCID 54362131, compound

HRID 726627Notes

Reaction equation

HRID 726627 reaction equation
Br[CH2:2][C:3]1[C:12]([CH2:13][Br:14])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[P:15]([O:20]C)([O:18][CH3:19])[O:16][CH3:17]>C1(C)C=CC=CC=1>[Br:14][CH2:13][C:12]1[C:3]([CH2:2][P:15]([O:18][CH3:19])([O:16][CH3:17])=[O:20])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 8472Trimethyl phosphiteHCID 22721471HCID 22721471, compound

Product 1

HCID 54362131HCID 54362131, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2,3-di(bromomethyl)quinoline (0.50 g, 1.4 mmol) and trimethyl phosphite (0.18 ml, 1.4 mmol) was refluxed in toluene for 4 hours. The reaction mixture was then concentrated in vacuo and the residue was flash chromatographed on silica gel. Elution with ethyl acetate afforded 0.35 g of 3-bromomethyl-2-(dimethylphosphonomethyl)quinoline.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customchromatographed on silica gel
  3. washElution with ethyl acetate

Sources & evidence

ORD record
ord-7a5d45060a674ec6961e02928de864c8
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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