Hydrogen Peroxide → 5-Bromo-2-carboxypyridine 1-oxide

HRID 709598Notes

Reaction equation

HRID 709598 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.NC(N)=[O:13].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N+:6]([O-:13])[CH:7]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1176UreaHCID 9845Trifluoroacetic anhydrideHCID 6085445-Bromopyridine-2-carboxylic acid

Product 1

HCID 684639675-Bromo-2-carboxypyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-bromopicolinic acid (25.0 g) and urea. hydrogen peroxide adduct (20.0 g) in acetonitrile (200 mL) was added trifluoroacetic anhydride (50 ml) at 0° C., and the mixture was stirred for 30 min. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The crude crystals were recrystallized from diethyl ether to give the title compound (19.6 g) as white crystals.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude crystals were recrystallized from diethyl ether

Sources & evidence

ORD record
ord-a40b594ad5e24cf3bf100b3b5138a287
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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