N,N'-Dimethylethylenediamine → 4-Methanesulfonyl-2-methoxyphenol

Temperature

130 °C

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%).

1. temperatureto cool to room temperature
2. filtrationThe resulting mixture was filtered through Celite pad and to the filtrate
3. additionwas added 2N hydrochloric acid
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed sequentially with water and brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→1/1)

ORD record

ord-ce1fe5281234494d821e78c584a38426

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08536176B2