反応 #998632

反応方程式

4-methylbenzenethiol

sodium hydride

methanesulfonic acid 3,3,3-trifluoro-2-methyl-2-trifluoromethylpropyl ester

→

desired intermediate

収率 66.2%

1-Methyl-4-(3,3,3-trifluoro-2-methyl-2-trifluoromethylpropylthio)benzene

収率 66.2%

溶媒

DMF

water

DMF

反応条件

後処理

1. 1
   温度cool the mixture to ambient temperature
2. 2
   抽出Extract three times with EtOAc
3. 3
   乾燥dry over anhydrous Na2SO4
4. 4
   濃縮concentrate in vacuo
5. 5
   その他Purify by chromatography on silica gel eluting with hexane

実験手順

In a sealed tube dissolve 4-methylbenzenethiol (4.13 g, 33.2 mmol) in DMF (20 mL) at ambient temperature. Add portionwise with stirring sodium hydride (899 mg, 37.5 mmol) followed by tetrabutylammonium iodide (82 mg, 0.22 mmol) and a solution of methanesulfonic acid 3,3,3-trifluoro-2-methyl-2-trifluoromethylpropyl ester (6.16 g, 22.5 mmol) in DMF (10 mL). Stir at 150° C. overnight, cool the mixture to ambient temperature and dilute cautiously with water. Extract three times with EtOAc, dry over anhydrous Na2SO4, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane to give the desired intermediate as a yellow oil (4.5 g, 62%).

出典