Hydrogen Peroxide → Diphenyltrifluoromethylphosphine oxide

HRID 1085321Notes

Reaction equation

HRID 1085321 reaction equation
[C:1]1([P:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:18]O.O>CC(C)=O>[C:1]1([P:7](=[O:18])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([F:11])([F:9])[F:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 12487824Diphenyl(trifluoromethyl)phosphane

Product 1

HCID 20061876Diphenyltrifluoromethylphosphine oxideYield 80.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1.0g (3.9 mmol) of diphenyltrifluoromethylphosphine (4) in 5 mL of acetone was treated with 0.5 mL (4.9 mmol) of 30% hydrogen peroxide. Within a few minutes an exothermic reaction occurred which caused the solution to reflux. After this had subsided, the solution was allowed to stand for 4 hours at room temperature and poured into 15 mL of water. The resulting aqueous mixture was extracted with three 10 mL portions of cichloromethane. The organic layers were combined, dried (MgSO4), and concentrated to give 0.85g (80% yield) of diphenyltrifluoromethylphosphine oxide as a colorless liquid: 19F NMR (CDCl3 relative to CF3CO2H) 5.86 ppm (d, JPF =89 Hz); mass spectrum (70 eV) m/z (relative intensity) 201 (100, M-CF3), 77 (23), 51 (16).

Workup

  1. customWithin a few minutes an exothermic reaction
  2. temperatureto reflux
  3. extractionThe resulting aqueous mixture was extracted with three 10 mL portions of cichloromethane
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bec4e1a5b2e749de9ea1e86b02aa7d8c
Source dataset
uspto-grants-1991_04
Patent number
US05008417

Reaction notes

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