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Triisopropyl phosphite → 5-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl-phosphonic acid, diisopropyl ester

HRID 462650
Notes
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Reaction equation

HRID 462650 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10](Cl)=[O:11].[P:25]([O:34]C(C)C)([O:30][CH:31]([CH3:33])[CH3:32])[O:26][CH:27]([CH3:29])[CH3:28].P([O-])([O-])[O-]>CCOCC>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([P:25](=[O:34])([O:30][CH:31]([CH3:33])[CH3:32])[O:26][CH:27]([CH3:29])[CH3:28])=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8304Triisopropyl phosphiteHCID 107908PhosphiteHCID 30177655-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chloride

Product 1

HCID 867400945-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl-phosphonic acid, diisopropyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent
2×

Procedure

To a stirred solution of 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride (3.8 g, 0.01 mole) in ether (100 ml) was added triisopropyl phosphite (2.1 g, 0.01 mole). The reaction was refluxed for one hour and the disappearance of phosphite monitored by v.p.c.. The ether was stripped off and the resulting oil placed under vacuum (1.0 mm) at 40° C. for two hours. The resulting amber liquid amounted to 5.2 g.

Workup

  1. temperatureThe reaction was refluxed for one hour

Sources & evidence

ORD record
ord-d663a8a07cc54c2ca4b3463d9951d83c
Source dataset
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04517010

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes