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

HRID 486267Notes

Reaction equation

HRID 486267 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 The solvent
  5. concentrationis concentrated

Sources & evidence

ORD record
ord-1972b1ffdc714f978cbe9c26680ec3a4
Source dataset
uspto-grants-1994_03
Patent number
US05290934

Reaction notes

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