Water → 4-Bromo-3-fluorobenzoic acid

HRID 394887Notes

Reaction equation

HRID 394887 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].[OH-:10].[Na+].[K].[OH2:13]>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:13])=[O:10])=[CH:4][C:3]=1[F:9]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5732804-Bromo-3-fluorotolueneHCID 5462222Potassium

Product 1

HCID 27733414-Bromo-3-fluorobenzoic acidYield 86.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-bromo-3-fluorotoluene (15.0 g, 79.35 mmol) and sodium hydroxide (3.3 g, 82.53 mmol) in pyridine (80 ml) and water (160 ml) was stirred at reflux. Potassium permanganese (52.7 g, 333.28 mmol) was added to the mixture over 30 min. The resulting suspension was heated at reflux for 3 h. The mixture was filtered through celite. The celite was washed with hot water, followed by ethyl acetate. The cooled aqueous layer was acidified to pH 1 with conc.HCl and extracted with ethyl acetate. The extracts was dried (MgSO4) and concentrated to afford 15.0 g (86.3%) of the titled compound as a white crystal. The compound was used for the next reaction directly.

Workup

  1. temperatureat reflux
  2. temperatureThe resulting suspension was heated
  3. temperatureat reflux for 3 h
  4. filtrationThe mixture was filtered through celite
  5. washThe celite was washed with hot water
  6. extractionHCl and extracted with ethyl acetate
  7. dry with materialThe extracts was dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e8cc5c2dedfd43cf8369f8683ebd442a
Source dataset
uspto-grants-2003_08
Patent number
US06603008B1

Reaction notes

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