Hydrogen Peroxide → Bis(4-bromophenyl)phenylphosphine oxide

HRID 1920610Notes

Reaction equation

HRID 1920610 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([P:8]([C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.OO.S([O-])([O-])=[O:25].[Na+].[Na+]>C(OCC)(=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([P:8](=[O:25])([C:15]2[CH:16]=[CH:17][C:18]([Br:21])=[CH:19][CH:20]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 10364804bis(4-bromophenyl)phenylphosphine

Product 1

HCID 15469924Bis(4-bromophenyl)phenylphosphine oxide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

10.05 g (24 mmol) of bis(4-bromophenyl)phenylphosphine were dissolved in 200 ml of ethyl acetate in a 500 ml four-necked flask with internal thermometer, mechanical stirrer, reflux condenser and dropping funnel and cooled to an internal temperature of 5° C. A solution of 2.25 ml (26.4 mmol) of H2O2 (35%) in 17.5 ml of water was added dropwise over the course of 30 min., and the mixture was stirred at room temperature for a further 12 h. 25 ml of saturated sodium sulfite solution were subsequently added, the organic phase was separated off, washed twice with saturated sodium sulfite solution and dried over sodium sulfate. The solvent was removed under reduced pressure. The purification was carried out firstly by column chromatography on silica using a solvent mixture of initially hexane:ethyl acetate 2:1 to hexane:ethyl acetate 1:1. Further purification was carried out by recrystallisation from heptane/toluene, giving 6.5 g of product in a purity of 99.7% (according to HPLC). 1H-NMR (500 MHz, CDCl3): [ppm] 7.46-7.66 (m). 31P-NMR (CDCl3): [ppm] 28.40.

Workup

  1. temperaturereflux condenser
  2. customthe organic phase was separated off
  3. washwashed twice with saturated sodium sulfite solution
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe purification
  7. additiona solvent mixture of initially hexane:ethyl acetate 2:1 to hexane:ethyl acetate 1:1
  8. customFurther purification
  9. customwas carried out by recrystallisation from heptane/toluene

Sources & evidence

ORD record
ord-53fab39c4508479189554bc38af587ac
Source dataset
uspto-grants-2012_05
Patent number
US08173276B2

Reaction notes

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