Reaction #302898

Reaction equation

methyl 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoate

sodium methoxide

→

methyl 2-methoxy-3-methylthio-4-(trifluoromethyl)benzoate

Yield 18.3%

Solvents

methanol

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureunder reflux for 6 h
3. 3
   ConcentrationFor work-up, the mixture was concentrated on a rotary evaporator
4. 4
   Extractionthe mixture was extracted with dichloromethane
5. 5
   OtherThe organic phase was dried
6. 6
   Extractionextracted with ethyl acetate
7. 7
   OtherThe organic phase was dried

Procedure

A mixture of 19.9 g (74.2 mmol) of methyl 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoate and 40.1 g (30% by weight, 223 mmol) of sodium methoxide in 250 ml of methanol was heated under reflux for 6 h. For work-up, the mixture was concentrated on a rotary evaporator, the residue was taken up in water and the mixture was extracted with dichloromethane. The organic phase was dried and the filtrate was freed from the solvent. This gave 15.9 g of methyl 2-methoxy-3-methylthio-4-(trifluoromethyl)benzoate as residue. The aqueous phase from the extractive work-up was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was dried and the filtrate was freed from the solvent. This gave an additional 3.80 g of methyl 2-methoxy-3-methylthio-4-(trifluoromethyl)benzoate as residue.

Source