Water → Diethyl [4-(diphenylphosphanyl)phenyl]phosphonate

HRID 2392846Notes

Reaction equation

HRID 2392846 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([P-:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[K+].F[C:16]1[CH:21]=[CH:20][C:19]([P:22](=[O:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])=[CH:18][CH:17]=1.O>C1COCC1.[S].[P]>[C:8]1([P:7]([C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)[C:16]2[CH:21]=[CH:20][C:19]([P:22](=[O:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])=[CH:18][CH:17]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11042360KPPh2HCID 13508438Diethyl (4-fluorophenyl)phosphonate

Product 1

HCID 15243843Diethyl [4-(diphenylphosphanyl)phenyl]phosphonateYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178527701HCID 178527701, compoundSolvent

Conditions

Temperature
23 °C

Procedure

25.8 ml (12.9 mmol) of potassium diphenylphosphide solution in THF (manufacturer: Aldrich) are added dropwise at -5° C. to a solution of 3.09 g (13.2 mmol) of diethyl 4-fluorophenylphosphonate, prepared as described in Phosphorus Sulfur 1980, 9(2), 197.202, in 20.0 ml of THF. After stirring for 19 hours at 23° C., the mixture is hydrolyzed by adding 20 ml of degassed water and stirring for 15 min. After extraction with ethyl acetate, and drying the organic phase over Na2SO4, the mixture is concentrated on a rotary evaporator. 4.20 g of diethyl 4-diphenylphosphinophenylphosphonate (82% of theory) are obtained in the form of a pale yellow oil.

Workup

  1. customprepared
  2. stirringstirring for 15 min
  3. extractionAfter extraction with ethyl acetate
  4. dry with materialdrying the organic phase over Na2SO4
  5. concentrationthe mixture is concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-f11c0f8b8bcd4d368d938c8c3361d411
Source dataset
uspto-grants-1998_09
Patent number
US05801263

Reaction notes

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