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

HRID 2394951Notes

Reaction equation

HRID 2394951 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-d15f36c42bef46bab5554e397a46ea06
Source dataset
uspto-grants-1998_09
Patent number
US05811576

Reaction notes

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