Reaktion #11003

Reaktionsgleichung

Sodium thiomethoxide

Methyl 2-nitro-4trifluoromethylbenzoate

Methyl 2-Nitro-4-trifluoromethylbenzoate

→

6a

Ausbeute 103.9%

Methyl 2-Methylthio-4-trifluoromethylbenzoate

Ausbeute 103.9%

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONadded to the mixture
2. 2
   Sonstigeto completely consume 5a
3. 3
   workup.ADDITIONThe reaction mixture was diluted with ethyl acetate and water
4. 4
   workup.ADDITIONthe layers were thoroughly mixed
5. 5
   Sonstigeseparated
6. 6
   TrocknenThe organic layer was dried over Na2SO4
7. 7
   Einengenconcentrated

Vorschrift

Sodium thiomethoxide (91 mg; 1.3 mmol; 1.3 equiv) was dissolved in water (0.34 mL). Tetrabutylammonium bromide (48 mg; 0.15 mmol; 0.15 equiv) was added. Methyl 2-nitro-4trifluoromethylbenzoate (5a; 249 mg; 1.0 mmol) was dissolved in toluene and added to the mixture. The reaction mixture was stirred at ambient temperature for 1 h to completely consume 5a according to gas chromatography (GC) analysis. The reaction mixture was diluted with ethyl acetate and water and the layers were thoroughly mixed and then separated. The organic layer was dried over Na2SO4 and concentrated to afford 0.26 g of 6a which contained a small amount of tetrabutylammonium bromide. The crude product was filtered through a pad of flash silica gel to afford 226 mg (90%) of 6a.

Quelle