Benzene, 2-chloro-1-(3,4-dinitrophenoxy)-4-(trifluoromethyl)- → methyl P-methyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate

HRID 1284416

Reaction equation

HRID 1284416 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.ClC1C([N+]([O-])=O)C(C2C=CC=CC=2C(F)(F)F)([N+]([O-])=O)C=CC=1OC1C=CC([N+]([O-])=O)(C2C=CC=CC=2C(F)(F)F)C([N+]([O-])=O)C=1Cl.[CH3:72][P:73]([O:76]C)[O:74][CH3:75]>C(#N)C>[CH3:72][P:73]([C:7]1[CH:6]=[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:10]=[CH:9][C:8]=1[N+:11]([O-:13])=[O:12])(=[O:76])[O:74][CH3:75]

Participants

5

Reactant 3

HCID 156238Benzene, 2-chloro-1-(3,4-dinitrophenoxy)-4-(trifluoromethyl)-HCID 4187293Dimethyl methylphosphoniteHCID 867405852-Chloro-alpha,alpha,alpha-trifluoro-p-tolyl-3,4-dinitrophenyl ether

Product 1

HCID 13564436methyl P-methyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(2-chloro-4-trifluoromethylphenoxy)-1,2-dinitrobenzene, (2-chloro-α,α,α-trifluoro-p-tolyl-3,4-dinitrophenyl ether) (1.2 g, 3.31 mmol) and dimethyl methylphosphonite (0.57 g, 5.3 mmol) in 3 ml of acetonitrile is refluxed overnight. The mixture is concentrated and the residue is purified by column chromatography (silica gel, eluting with 3% ethyl acetate/hexane) to yield methyl P-methyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate.

Workup

  1. temperatureis refluxed overnight
  2. concentrationThe mixture is concentrated
  3. customthe residue is purified by column chromatography (silica gel, eluting with 3% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3db1e4a4f26946b285cbce4977c51fba
Source dataset
uspto-grants-1986_01
Patent number
US04563310

Linked notes

Loading…