Reaction #1382

Reaction equation

methyl 2-methyl-3-fluoro-4,6-dibromobenzoate

ethanol

sodium hydroxide

→

2-methyl-3-fluoro-4,6-dibromobenzoic acid

Yield 84.4%

Solvents

water

Conditions

Workup

1. 1
   Temperaturethe mixture is refluxed for 2 hours
2. 2
   TemperatureAfter cooling
3. 3
   Extractionextracted with diethyl ether
4. 4
   Extractionextracted with diethyl ether
5. 5
   ConcentrationThe solvent is concentrated

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.

Source