Reaktion #302898

ord-912ba68d57b54d7b926afaffcb88c6da

Reaktionsgleichung

COC(=O)c1ccc(C(F)(F)F)c(SC)c1F
methyl 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoate
C[O-].[Na+]
sodium methoxide
COC(=O)c1ccc(C(F)(F)F)c(SC)c1OC
methyl 2-methoxy-3-methylthio-4-(trifluoromethyl)benzoate
Ausbeute 18.3%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturwas heated
  2. 2
    Temperaturunder reflux for 6 h
  3. 3
    EinengenFor work-up, the mixture was concentrated on a rotary evaporator
  4. 4
    Extraktionthe mixture was extracted with dichloromethane
  5. 5
    SonstigeThe organic phase was dried
  6. 6
    Extraktionextracted with ethyl acetate
  7. 7
    SonstigeThe organic phase was dried

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08193121B2uspto-grants-2012_06