Hydrogen Peroxide → (3-BroMo-2,6-diMethoxy-4-pyridyl)diphenylphosphine oxide

HRID 1419501Notes

Reaction equation

HRID 1419501 reaction equation
[CH3:1][O:2][C:3]1[C:8]([Br:9])=[C:7]([P:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[C:5]([O:23][CH3:24])[N:4]=1.[OH:25]O>CC(C)=O>[CH3:1][O:2][C:3]1[C:8]([Br:9])=[C:7]([P:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:25])[CH:6]=[C:5]([O:23][CH3:24])[N:4]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 15404605HCID 15404605, compound

Product 1

HCID 44591520(3-BroMo-2,6-diMethoxy-4-pyridyl)diphenylphosphine oxideYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A round bottom flask with a magnetic stirring bar was charged with 2,6-dimethoxy-3-bromo-4-(diphenylphosphino)pyridine (4.96 g) and 50 mL acetone. To this solution was slowly added approximately 35% hydrogen peroxide (33.9 mL). The reaction was monitored by thin-layer chromatography. The product was extracted with 3×20 mL dichloromethane. The combined extract was dried with anhydrous magnesium sulfate and was concentrated in vaccuo to give a crude product which was purified by column chromatography (silica gel, CHCl3 : ethyl acetate=1:1 with 5% NEt3) to give 5.15 g pure product (96% of theoretical yield).

Workup

  1. extractionThe product was extracted with 3×20 mL dichloromethane
  2. extractionThe combined extract
  3. dry with materialwas dried with anhydrous magnesium sulfate
  4. concentrationwas concentrated in vaccuo
  5. customto give a crude product which
  6. customwas purified by column chromatography (silica gel, CHCl3 : ethyl acetate=1:1 with 5% NEt3)

Sources & evidence

ORD record
ord-57500677f8494cd1bc3ee777a5127e54
Source dataset
uspto-grants-1999_03
Patent number
US05886182

Reaction notes

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