Hydrogen Peroxide → 4-Bromo-2-fluorobenzoic acid

HRID 586807Notes

Reaction equation

HRID 586807 reaction equation
OO.[Br:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([F:12])[CH:5]=1.Cl([O-])=[O:14].[Na+].OS([O-])(=O)=O.[K+]>C(#N)C.O>[Br:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]([OH:14])=[O:9])=[C:6]([F:12])[CH:5]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 516920Potassium bisulfateHCID 23668197Sodium Chlorite

Product 1

HCID 3026814-Bromo-2-fluorobenzoic acidYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of water (3 ml) and acetonitrile (5 ml) were added Na2HPO4.12H2O (0.11 g), 31% aqueous hydrogen peroxide (0.34 g, 3.1 mmol), 4-bromo-2-fluorobenzaldehyde (0.41 g, 2.0 mmol) and sodium chlorite (0.27 g, 3.0 mmol), successively, and stirred at room temperature for 1 hour. The reaction solution was poured into 5% KHSO4, extracted three times with ethyl acetate and the combined extracts were dried over MgSO4. The solvent was evaporated under a reduced pressure to give the title compound (0.42 g; 96%).

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialthe combined extracts were dried over MgSO4
  3. customThe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-e26f25b87da64e2087baf87037b3408a
Source dataset
uspto-grants-2005_08
Patent number
US06936736B2

Reaction notes

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