Potassium Carbonate → Diethyl 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxymethyl-phosphonate

HRID 1263186Notes

Reaction equation

HRID 1263186 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:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([N+]([O-])=O)[CH:6]=1.[OH:25][CH2:26][P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][C:3]2[CH:17]=[CH:18][C:19]([C:21]([F:24])([F:23])[F:22])=[CH:20][C:2]=2[Cl:1])=[CH:6][C:7]=1[O:25][CH2:26][P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76513Diethyl phosphonomethanolHCID 156238Benzene, 2-chloro-1-(3,4-dinitrophenoxy)-4-(trifluoromethyl)-

Product 1

HCID 13343564Diethyl 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxymethyl-phosphonate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-(2-chloro-4-trifluoromethylphenoxy)-1,2-dinitrobenzene (500 mg, 1.38 mmol), diethyl hydroxymethylphosphonate (295 mg, 1.66 mmol) and potassium carbonate (285 mg, 2.07 mmol) in 2-butanone (5 ml) is heated under reflux for 6 hours. After cooling, the reaction mixture is filtered, and the filtrate is concentrated to dryness. The crude product is purified by preparative thin layer chromatography (prep. TLC) (silica gel, developed with 50% ethyl acetate/hexane) to give diethyl 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxymethyl-phosphonate.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture is filtered
  5. concentrationthe filtrate is concentrated to dryness
  6. customThe crude product is purified by preparative thin layer chromatography (prep. TLC) (silica gel, developed with 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9a737702eb234e2ba2233487cccb8101
Source dataset
uspto-grants-1984_06
Patent number
US04456464

Reaction notes

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