4-Nitrophenol → 4-Nitrophenyl P-methyl-P-phenylphosphinate

HRID 1726051Notes

Reaction equation

HRID 1726051 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].[CH3:13][P:14](Cl)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15]>O1CCCC1.O>[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][P:14]([CH3:13])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])=[CH:8][CH:7]=1)([O-:5])=[O:4]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 21983Methyl(phenyl)phosphinoyl chlorideHCID 24758Sodium hydride

Product 1

HCID 1147964-Nitrophenyl P-methyl-P-phenylphosphinateYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

The methylphenylphosphinic acid 4-nitrophenyl ester is prepared in the following way: A suspension of 173 mg of NaH at 50% in oil, in 2 ml of anhydrous tetrahydrofuran, is stirred at ambient temperature under argon. A solution of 500 mg of 4-nitrophenol in 2 ml of anhydrous tetrahydrofuran is added dropwise at ambient temperature. After stirring for approximately 1 hour at ambient temperature, a solution of 630 mg of methylphenylphosphinic chloride in 2 ml of anhydrous tetrahydrofuran is added dropwise over about ten minutes. After stirring for approximately 2 hours, the reaction medium is diluted with 20 ml of distilled water and the aqueous phase is extracted with 2×20 ml of dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered, and concentrated under reduced pressure in a rotary evaporator. 995 mg of methylphenylphosphinic acid 4-nitrophenyl ester are obtained with a purity of 50%.

Workup

  1. customThe methylphenylphosphinic acid 4-nitrophenyl ester is prepared in the following way
  2. stirringAfter stirring for approximately 2 hours
  3. extractionthe aqueous phase is extracted with 2×20 ml of dichloromethane
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure in a rotary evaporator

Sources & evidence

ORD record
ord-bcd5ba3fa5654a029e4f5bcc3b1d88c4
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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