1-Bromo-4-fluorobenzene → Bis(4-fluorophenyl)phenylphosphine oxide

HRID 1609148Notes

Reaction equation

HRID 1609148 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.Cl[P:11](=[O:19])(Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(OCC)C>[F:9][C:6]1[CH:7]=[CH:8][C:3]([P:11](=[O:19])([C:3]2[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 99931-Bromo-4-fluorobenzeneHCID 69990Phenylphosphonic dichlorideHCID 5462224Magnesium

Product 1

HCID 3532979Bis(4-fluorophenyl)phenylphosphine oxideYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A mixture of anhydrous ethylether and dried magnesium 5 g was put in a reaction vessel, into which a solution of parabromofluorobezene 35 g dissolved in anhydrous ethylether 50 ml subsequently was added slowly to prepare a Grignard reagent. Into this Grignard reagent, a solution of dichlorophenylphosphine oxide 19.5 g dissolved in anhydrous ethylether was added for a reaction. After performing the reaction, the solution was washed with distilled water and moisture was removed therefrom with a drying agent. Thereafter, the resulting solution was concentrated under a reduced pressure and was vacuum-distilled to give 25.77 g of bis(4-fluorophenyl)phenylphosphine oxide, which was then subjected to the treatment of infrared spectrum analysis and NMR spectrum analysis to insure the existence of P=O and --P--C6H4 -- groups therein.

Workup

  1. customwas put in a reaction vessel, into which
  2. additionsubsequently was added slowly
  3. additionwas added for a reaction
  4. customthe reaction
  5. washthe solution was washed with distilled water and moisture
  6. customwas removed
  7. concentrationThereafter, the resulting solution was concentrated under a reduced pressure
  8. distillationwas vacuum-distilled

Sources & evidence

ORD record
ord-912ee64ac749427a94a2c812018f09cd
Source dataset
uspto-grants-1995_03
Patent number
US05399654

Reaction notes

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