Reacción #70430

Ecuación de reacción

4-bromo-2-methoxyphenol

sodium methanesulfinate

N,N′-dimethylethylenediamine

ethyl acetate

→

title compound

Rendimiento 52.0%

4-Methanesulfonyl-2-methoxyphenol

Rendimiento 52.0%

Disolventes

dimethyl sulfoxide

water

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%).

Fuente