Trimethyl phosphite → 6,7-Dichloro-3-dimethylphosphonomethyl-2-bromoquinoline

HRID 726645Notes

Reaction equation

HRID 726645 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([Br:13])[C:6]([CH2:14]Br)=[CH:5]2.[CH3:16][O:17][P:18]([O:21]C)[O:19][CH3:20]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([Br:13])[C:6]([CH2:14][P:18]([O:19][CH3:20])([O:17][CH3:16])=[O:21])=[CH:5]2

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 197067206,7-Dichloro-2-bromo-3-bromomethylquinoline

Product 1

HCID 540461326,7-Dichloro-3-dimethylphosphonomethyl-2-bromoquinoline

Procedure

A mixture of 6,7-dichloro-2-bromo-3-bromomethylquinoline (0.74 g, 2 mmol) and trimethylphosphite (5 ml) was heated at 80°-90° C. for 2-3h. Then the excess trimethylphosphite was removed in vacuo at 70°-80° C. and the oily residue was made crystalline by treating with hexane-ethyl ether (1:1). The crystalls were collected, washed with toluene and dried in vacuo to give 0.65 g of 6,7-dichloro-3-dimethylphosphonomethyl-2-bromoquinoline.

Workup

  1. temperaturewas heated at 80°-90° C. for 2-3h
  2. customThen the excess trimethylphosphite was removed in vacuo at 70°-80° C.
  3. additionby treating with hexane-ethyl ether (1:1)
  4. customThe crystalls were collected
  5. washwashed with toluene
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a0a4ca57d2c4442987f3ccc2be08b6c1
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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