Reaktion #70430

Reaktionsgleichung

4-bromo-2-methoxyphenol

sodium methanesulfinate

N,N′-dimethylethylenediamine

ethyl acetate

→

title compound

Ausbeute 52.0%

4-Methanesulfonyl-2-methoxyphenol

Ausbeute 52.0%

Lösungsmittel

dimethyl sulfoxide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature
2. 2
   FiltrationThe resulting mixture was filtered through Celite pad and to the filtrate
3. 3
   workup.ADDITIONwas added 2N hydrochloric acid
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe organic layer was washed sequentially with water and brine
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→1/1)

Vorschrift

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%).

Quelle