Реакция #11003

Уравнение реакции

Sodium thiomethoxide

Methyl 2-nitro-4trifluoromethylbenzoate

Methyl 2-Nitro-4-trifluoromethylbenzoate

→

6a

Выход 103.9%

Methyl 2-Methylthio-4-trifluoromethylbenzoate

Выход 103.9%

Растворители

water

toluene

Условия реакции

Обработка

1. 1
   workup.ADDITIONadded to the mixture
2. 2
   Другоеto 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
   Другоеseparated
6. 6
   СушкаThe organic layer was dried over Na2SO4
7. 7
   Концентрированиеconcentrated

Методика

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.

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