Methanesulfonyl chloride → S-(1,1-Dimethylethyl) methanesulfonothioate

Temperature

-60 °C

Tetrahydrofuran (100 ml) was added to sodium 2-methyl-2-propanethiolate (7.83 g, 69.8 mmol), and the mixture was cooled to −60° C. or lower. A solution of methanesulfonyl chloride (6.77 ml, 87.0 mmol) in tetrahydrofuran (50 ml) was added dropwise to this suspension over 25 minutes. The reaction solution was gradually warmed to room temperature over 2 hours and stirred at room temperature for additional 1 hour. The reaction solution was diluted with dichloromethane (300 ml) and washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to afford S-tert-butyl methanesulfonothioate (Compound SP684) (11.17 g, 76%). The obtained compound was confirmed based on the compound data described in Non patent literature (Inorganic Chemistry, 2010, 49, 8637-8644).

1. temperatureThe reaction solution was gradually warmed to room temperature over 2 hours
2. washwashed with saturated aqueous sodium bicarbonate and brine
3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure

ORD record

ord-5855c3283be94625b8a40b40bfd5841d

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409952B2