Hydrogen Peroxide → Tris(2-bromo-6-pyridyl)phosphine oxide

HRID 13634

Reaction equation

HRID 13634 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([P:8]([C:16]2[N:21]=[C:20]([Br:22])[CH:19]=[CH:18][CH:17]=2)[C:9]2[N:14]=[C:13]([Br:15])[CH:12]=[CH:11][CH:10]=2)[N:3]=1.[OH:23]O.O>C(Cl)(Cl)Cl>[Br:22][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([P:8](=[O:23])([C:9]2[N:14]=[C:13]([Br:15])[CH:12]=[CH:11][CH:10]=2)[C:4]2[N:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=2)[N:21]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 15190498Tris(2-bromo-6-pyridyl)phosphine

Product 1

HCID 21708779Tris(2-bromo-6-pyridyl)phosphine oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension, heated to boiling, of 50.2 g (100.0 mmol) of tris(2-bromo-6-pyridyl)phosphine in 500 ml of chloroform was admixed with intensive stirring dropwise with a mixture of 11 ml of 35% by weight H2O2 and 50 ml of water, which afforded a clear solution. After stirring under reflux for 5 h, the solution was allowed to cool to room temperature. The solution was washed with 500 ml of water, and the organic phase was removed and concentrated to 50 ml under reduced pressure. After standing for 2 h, the precipitated crystals were filtered off, washed three times with 100 ml of n-hexane and then dried at 70° C. under reduced pressure. The yield at a purity of 99.0% was 47.1 g (90.9%).

Workup

  1. temperatureA suspension, heated
  2. customafforded a clear solution
  3. temperatureunder reflux for 5 h
  4. washThe solution was washed with 500 ml of water
  5. customthe organic phase was removed
  6. concentrationconcentrated to 50 ml under reduced pressure
  7. filtrationthe precipitated crystals were filtered off
  8. washwashed three times with 100 ml of n-hexane
  9. customdried at 70° C. under reduced pressure
  10. customThe yield at a purity of 99.0%

Sources & evidence

ORD record
ord-2e008cd55780412e8f76fd39668f6b90
Source dataset
uspto-grants-2010_06
Patent number
US07728137B2

Linked notes

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