تفاعل #11003

معادلة التفاعل

Sodium thiomethoxide

Methyl 2-nitro-4trifluoromethylbenzoate

Methyl 2-Nitro-4-trifluoromethylbenzoate

→

6a

المردود 103.9%

Methyl 2-Methylthio-4-trifluoromethylbenzoate

المردود 103.9%

المذيبات

water

toluene

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONadded to the mixture
2. 2
   أخرىto 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
   أخرىseparated
6. 6
   تجفيفThe organic layer was dried over Na2SO4
7. 7
   تركيزconcentrated

الإجراء التجريبي

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.

المصدر