Triethyl phosphite → Fosarilate

HRID 2051751Notes

Reaction equation

HRID 2051751 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]Br.[P:18]([O:25]CC)([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]>>[Cl:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 920684-((6-Bromohexyl)oxy)-3-chloroanisole

Product 1

HCID 71756FosarilateYield 30.4%

Procedure

A mixture of 10 g (0.0313 mole) of 6-(2-chloro-4-methoxyphenoxy)hexyl bromide and 5.2 g (0.313 mole) of triethyl phosphite was heated at 180°-190° C. for two hours. The reaction mixture was distilled in vacuo, and the fraction (4.6 g) collected at 183°-185° C. (0.03 mm) was redistilled to give 3.6 g of diethyl [6-(2-chloro-4-methoxyphenoxy)hexyl]phosphonate, b.p. 195°-197° C. (0.005 mm).

Workup

  1. temperaturewas heated at 180°-190° C. for two hours
  2. distillationThe reaction mixture was distilled in vacuo
  3. customthe fraction (4.6 g) collected at 183°-185° C. (0.03 mm)
  4. distillationwas redistilled

Sources & evidence

ORD record
ord-96443e83b12e44008ac70a783e59376d
Source dataset
uspto-grants-1980_01
Patent number
US04182759

Reaction notes

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