Ethanol → 4,6-Dibromo-3-fluoro-2-methylbenzoic acid

HRID 864342Notes

Reaction equation

HRID 864342 reaction equation
[CH3:1][C:2]1[C:11]([F:12])=[C:10]([Br:13])[CH:9]=[C:8]([Br:14])[C:3]=1[C:4]([O:6]C)=[O:5].C(O)C.[OH-].[Na+]>O>[CH3:1][C:2]1[C:11]([F:12])=[C:10]([Br:13])[CH:9]=[C:8]([Br:14])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 189744684,6-Dibromo-3-fluoro-2-methyl-benzoic acid methylester

Product 1

HCID 146512824,6-Dibromo-3-fluoro-2-methylbenzoic acidYield 84.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methyl 2-methyl-3-fluoro-4,6-dibromobenzoate (75.5 g) are added ethanol (460 ml) and 10% aqueous solution of sodium hydroxide (460 ml) and the mixture is refluxed for 2 hours. After cooling, the reaction mixture is diluted with water and extracted with diethyl ether. The aqueous layer is made acidic with conc. hydrochloric acid and extracted with diethyl ether. The solvent is concentrated to give 2-methyl-3-fluoro-4,6-dibromobenzoic acid (61 g), m.p. 144°-146° C.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with diethyl ether
  4. extractionextracted with diethyl ether
  5. concentrationThe solvent is concentrated

Sources & evidence

ORD record
ord-a5ee737640f948f0b7b24c43afef175d
Source dataset
uspto-grants-1996_10
Patent number
US05563138

Reaction notes

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