1-Diethoxyphosphorylethanol → Diethyl 1-[2-[5-(o-chloro-p-trifluoromethyl-phenoxy)-2-nitrophenoxy]-propionyloxy]-ethylphosphonate

HRID 414651Notes

Reaction equation

[Cl:1][C:2]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:17]([O-:19])=[O:18])=[C:9]([CH:16]=1)[O:10][CH:11]([CH3:15])[C:12](Cl)=[O:13].[OH:28][CH:29]([P:31](=[O:38])([O:35][CH2:36][CH3:37])[O:32][CH2:33][CH3:34])[CH3:30]>>[Cl:1][C:2]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:17]([O-:19])=[O:18])=[C:9]([CH:16]=1)[O:10][CH:11]([CH3:15])[C:12]([O:28][CH:29]([P:31](=[O:38])([O:32][CH2:33][CH3:34])[O:35][CH2:36][CH3:37])[CH3:30])=[O:13]

Participants

Reactant 2

HCID 5191091-Diethoxyphosphorylethanol

HCID 131006842-[2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl Chloride

Product 1

HCID 21281541Diethyl 1-[2-[5-(o-chloro-p-trifluoromethyl-phenoxy)-2-nitrophenoxy]-propionyloxy]-ethylphosphonate

Procedure

by using 2-[5-(o-chloro-p-trifluoromethyl-phenoxy)-2-nitrophenoxy]-propionyl chloride and diethyl 1-hydroxyethylphosphonate there is obtained diethyl 1-[2-[5-(o-chloro-p-trifluoromethyl-phenoxy)-2-nitrophenoxy]-propionyloxy]-ethylphosphonate, 1H-NMR (CDCl3, 400 MHz) 7.93 ppm and 7.92 ppm (2d, 1H), 7.79 ppm (d, 1H), 7.51-7.55 ppm (m, 1H), 7.23 ppm and 7.19 ppm (2d, 1H), 6.68 ppm and 6.58 ppm (2d, 1H), 6.53 ppm and 6.46 ppm (2q, 1H), 5.31 ppm and 5.29 ppm (2q, 1H), 4.88 and 4.85 ppm (2q, 1H), 4.21-4.05 ppm (m, 4H), 1.73 ppm and 1.72 ppm (2d, 3H), 1.45 ppm and 1.42 ppm (2q, 3H), 1.36-1.26 ppm (m, 6H).

Sources & evidence

ORD record: ord-859c9108d6424732b492ee1f2f21015d
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04792616

Reaction notes

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