Dimethyl Sulfate → (Bis-methylsulfanyl-methylene)-methyl-sulfonium tetrafluoroborate salt
Reaction equation
S(OC)(O[CH3:5])(=O)=O.[C:8](=[S:13])([S:11][CH3:12])[S:9][CH3:10].[F:14][B-:15]([F:18])([F:17])[F:16].[H+]>C(#N)C>[F:14][B-:15]([F:18])([F:17])[F:16].[CH3:10][S:9][C:8](=[S+:13][CH3:5])[S:11][CH3:12]Participants
5
Conditions
- Temperature
- 90 °C
Procedure
Dimethyl sulfate (22.84 mL, 240 mmol) and dimethyl trithiocarbonate (26.48 mL, 240 mmol) were added to acetonitrile (80 mL). The resultant dark yellow solution was heated to 90° C. for 2 hours. The mixture was then allowed to cool to 55° C. and then a solution of tetrafluoroboric acid (54% in diethyl ether, 48 mL) was added over 5 min time. The resultant solution was stirred for an additional 15 min, followed by pouring it into a solution of ice-cold diethyl ether (600 mL). The white solid that formed was collected and washed with diethyl ether (3×50 mL) and dried in a vacuum oven to provide (bis-methylsulfanyl-methylene)-methyl-sulfonium tetrafluoroborate salt (47.3 g, 83%) as a colorless solid.
Workup
- temperatureto cool to 55° C.
- customThe white solid that formed
- customwas collected
- washwashed with diethyl ether (3×50 mL)
- customdried in a vacuum oven
Sources & evidence
- ORD record
- ord-f6e0da03055e484ca67cfba9e4592ed2
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951800B2
Reaction notes
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