Hydrogen Peroxide → 4-Methoxyphenylphenylpyrenylphosphine oxide

HRID 1967657Notes

Reaction equation

HRID 1967657 reaction equation
[C:1]1([P:17]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.[OH:32]O>C(Cl)(Cl)Cl>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([P:17](=[O:32])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:1]2[C:14]3[C:15]4=[C:16]5[C:11](=[CH:12][CH:13]=3)[CH:10]=[CH:9][CH:8]=[C:7]5[CH:6]=[CH:5][C:4]4=[CH:3][CH:2]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 541970834-Methoxyphenylphenylpyrenylphosphine

Product 1

HCID 581129154-Methoxyphenylphenylpyrenylphosphine oxideYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Pyrenylphenyl-4-methoxyphenylphosphine [Va] (1.68 g, 4.03 mmol) was dissolved in 25 mL of chloroform, and 5 mL of hydrogen peroxide was slowly added dropwise to the solution. The mixture was stirred for 5 minutes and then the reaction was quenched with 25 mL of 10% sodium thiosulfate. The mixture was extracted with chloroform (20 mL×3). The organic layer was dried over sodium sulfate and concentrated on an evaporator to give white crystals in 97% yield. The white crystals obtained were identified by 1H-NMR, 31P-NMR and 13C-NMR.

Workup

  1. customthe reaction was quenched with 25 mL of 10% sodium thiosulfate
  2. extractionThe mixture was extracted with chloroform (20 mL×3)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated on an evaporator
  5. customto give white crystals in 97% yield
  6. customThe white crystals obtained

Sources & evidence

ORD record
ord-14cf8390c2bb43fb9a98e4b65a0f3273
Source dataset
uspto-grants-2013_04
Patent number
US08420865B2

Reaction notes

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