反応 #70430

反応方程式

4-bromo-2-methoxyphenol

sodium methanesulfinate

N,N′-dimethylethylenediamine

ethyl acetate

→

title compound

収率 52.0%

4-Methanesulfonyl-2-methoxyphenol

収率 52.0%

溶媒

dimethyl sulfoxide

water

反応条件

後処理

1. 1
   温度to cool to room temperature
2. 2
   ろ過The resulting mixture was filtered through Celite pad and to the filtrate
3. 3
   workup.ADDITIONwas added 2N hydrochloric acid
4. 4
   抽出extracted with ethyl acetate
5. 5
   洗浄The organic layer was washed sequentially with water and brine
6. 6
   乾燥dried over anhydrous sodium sulfate
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→1/1)

実験手順

A mixture of 4-bromo-2-methoxyphenol (500 mg, 2.46 mmol), sodium methanesulfinate (1 g, 9.84 mmol), copper(I) trifluoromethanesulfonate benzene complex (124 mg, 0.25 mmol) and N,N′-dimethylethylenediamine (53 μL, 0.49 mmol) in dimethyl sulfoxide (3 mL) was stirred overnight at 130° C. The mixture was allowed to cool to room temperature followed by the addition of ethyl acetate (8 mL) and water (8 mL). The resulting mixture was filtered through Celite pad and to the filtrate was added 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→1/1) to give the title compound as a white crystal (258 mg, yield 52%).

出典