Dimethylformamide → 2,2-dimethylpropionyloxymethyl P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate

HRID 1263179Notes

Reaction equation

HRID 1263179 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].[CH3:27][C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH2:32]Cl)=[O:30].C(N(CC)CC)C.CN(C)C=O>C(Cl)Cl>[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][CH2:32][O:31][C:29](=[O:30])[C:28]([CH3:35])([CH3:34])[CH3:27])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 87885Chloromethyl pivalateHCID 15589803P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinic acid

Product 1

HCID 155898042,2-dimethylpropionyloxymethyl P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinic acid (0.33 g, 0.80 mmol), chloromethyl 2,2-dimethylpropanoate (0.24 g, 1.60 mmol), triethylamine (0.22 ml) and dimethylformamide (DMF) (3 ml) is stirred at RT for 2 days. The reaction is then diluted with methylene chloride, washed, dried and evaporated to dryness, followed by purification by preparative thin layer chromatography (prep. TLC) (silica gel, eluting with 40% ethyl acetate/hexane) to yield 2,2-dimethylpropionyloxymethyl P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate.

Workup

  1. washwashed
  2. customdried
  3. customevaporated to dryness
  4. customfollowed by purification by preparative thin layer chromatography (prep. TLC) (silica gel, eluting with 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c760204e1b9448909dcc6aa872dc22af
Source dataset
uspto-grants-1984_06
Patent number
US04456465

Reaction notes

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