Trifluoroacetic anhydride → 5-Bromo-2-carboxypyridine 1-oxide

HRID 1049519Notes

Reaction equation

HRID 1049519 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

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 6085445-Bromopyridine-2-carboxylic acid

Product 1

HCID 684639675-Bromo-2-carboxypyridine 1-oxideYield 72.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension 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 obtained residue was 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 obtained residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-1720ff665032443fb9dff0a0343870bc
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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