Water → benzoyloxymethyl P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate

HRID 1263180Notes

Reaction equation

HRID 1263180 reaction equation
[CH2:1]([P:3]([C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[Cl:23])[CH:9]=[CH:8][C:7]=1[N+:24]([O-:26])=[O:25])(=[O:5])[OH:4])[CH3:2].[C:27]([O:35][CH2:36]Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C.O>CN(C=O)C>[CH2:1]([P:3]([C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:22])[F:21])=[CH:15][C:14]=2[Cl:23])[CH:9]=[CH:8][C:7]=1[N+:24]([O-:26])=[O:25])(=[O:4])[O:5][CH2:36][O:35][C:27](=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 79257Chloromethyl benzoateHCID 15589803P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinic acid

Product 1

HCID 15589805benzoyloxymethyl P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinic acid (0.40 g, 0.97 mmol), chloromethyl benzoate (0.23 g, 1.36 mmol) and triethylamine (0.27 g) in 4 ml of DMF is stirred at RT for 4 days. The reaction mixture is poured into water and extracted with methylene chloride. The combined extracts are washed, dried, evaporated to dryness and purified by prep. TLC (eluting with 50% ethyl acetate/hexane) to yield benzoyloxymethyl P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined extracts are washed
  3. customdried
  4. customevaporated to dryness
  5. custompurified by prep
  6. washTLC (eluting with 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b5c342ae4e694f66a1f40cc1eafb229f
Source dataset
uspto-grants-1984_06
Patent number
US04456465

Reaction notes

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