Triethyl phosphite → 2-Bromo-7-chloro-3-diethylphosphonomethyl-6-methylquinoline

HRID 726648Notes

Reaction equation

HRID 726648 reaction equation
[Br:1][C:2]1[C:11]([CH2:12]Br)=[CH:10][C:9]2[C:4](=[CH:5][C:6]([Cl:15])=[C:7]([CH3:14])[CH:8]=2)[N:3]=1.[CH2:16]([O:18][P:19]([O:23]CC)[O:20][CH2:21][CH3:22])[CH3:17]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:11]([CH2:12][P:19]([O:20][CH2:21][CH3:22])([O:18][CH2:16][CH3:17])=[O:23])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([Cl:15])=[C:7]([CH3:14])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 227450662-Bromo-3-bromomethyl-7-chloro-6-methylquinoline

Product 1

HCID 542836542-Bromo-7-chloro-3-diethylphosphonomethyl-6-methylquinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-bromo-3-bromomethyl-7-chloro-6-methylquinoline (4.2 g, 12 mmol), toluene (50 ml) and triethylphosphite (4.2 ml) was refluxed for 20 h. After cooling the solution was concentrated in vacuum and the product precipitated by the addition of hexane. The crystals were filtered off, washed with hexane and dried in vacuo to give 4.5 g of 2-bromo-7-chloro-3-diethylphosphonomethyl-6-methylquinoline.

Workup

  1. temperaturewas refluxed for 20 h
  2. temperatureAfter cooling the solution
  3. concentrationwas concentrated in vacuum
  4. customthe product precipitated by the addition of hexane
  5. filtrationThe crystals were filtered off
  6. washwashed with hexane
  7. customdried in vacuo

Sources & evidence

ORD record
ord-517e95cd09e240ff9acb26379f36ec3c
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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