Реакция #70430

Уравнение реакции

4-bromo-2-methoxyphenol

sodium methanesulfinate

N,N′-dimethylethylenediamine

ethyl acetate

→

title compound

Выход 52.0%

4-Methanesulfonyl-2-methoxyphenol

Выход 52.0%

Растворители

dimethyl sulfoxide

water

Условия реакции

Обработка

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

Методика

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%).

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