Diethyl methylphosphonite → ethyl P-methyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate

HRID 1284420Notes

Reaction equation

HRID 1284420 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.[CH3:25][P:26]([O:30]CC)[O:27][CH2:28][CH3:29]>C(#N)C>[CH3:25][P:26]([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:30])[O:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 85063Diethyl methylphosphoniteHCID 156238Benzene, 2-chloro-1-(3,4-dinitrophenoxy)-4-(trifluoromethyl)-

Product 1

HCID 54254448ethyl 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 (0.9 g, 2.48 mmol), diethyl methylphosphonite (0.5 g, 3.72 mmol) and acetonitrile (3 ml) is stirred at room temperature overnight. The reaction mixture is concentrated to dryness, and the residue is purified by preparative thin layer chromatography (silica gel, eluting with 50% ethyl acetate/hexane) to give ethyl P-methyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness
  2. customthe residue is purified by preparative thin layer chromatography (silica gel, eluting with 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c2ea13a7bc7043999137d6ae5252024c
Source dataset
uspto-grants-1986_01
Patent number
US04563310

Reaction notes

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