Hydrogen Peroxide → HCID 178488303, compound

HRID 656242Notes

Reaction equation

HRID 656242 reaction equation
OO.[CH3:3][O:4][C:5]1[C:6]([OH:11])=[N:7][CH:8]=[CH:9][CH:10]=1.S([O-])([O-])(=O)=S.[Na+].[Na+].[Br:19]Br.C(=O)([O-])[O-].[Na+].[Na+]>Br>[Br:19][C:8]1[N:7]=[C:6]([OH:11])[C:5]([O:4][CH3:3])=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 178492106HCID 178492106, compound

Product 1

HCID 178488303HCID 178488303, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

45 ml of hydrogen peroxide (15% strength) are added dropwise to a stirred solution of 152.5 mmol of 3-methoxypyridin-2-ol [20928-63-6] in 152 ml of hydrobromic acid (48% strength) at 70° C. over the course of one hour so that the temperature remains at 70° C. The mixture is stirred at this temperature for a further hour. It is then cooled to room temperature, and 1M sodium thiosulphate solution is added to the reaction solution until excess bromine is completely reduced (decolorization). Saturated sodium carbonate solution is then added to the resulting solution until the pH is 4. A solid precipitates and is filtered off. Further saturated sodium carbonate solution is added to the clear filtrate until the pH reaches 11. It is extracted with dichloromethane (3×), and the combined organic phases are dried with sodium sulphate and evaporated. The title compound is identified by means of the Rf from the residue by flash chromatography (SiO2 60 F).

Workup

  1. customremains at 70° C
  2. customA solid precipitates
  3. filtrationis filtered off
  4. additionFurther saturated sodium carbonate solution is added to the clear filtrate until the pH
  5. extractionIt is extracted with dichloromethane (3×)
  6. dry with materialthe combined organic phases are dried with sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-9ce92d1aa43342889c3d02b65fd3906f
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Reaction notes

Loading…