Hydrogen Bromide → Triphenylsulfonium Bromide

A 3.0 M solution of phenylmagnesium bromide in diethyl ether (50 ml, 0.15 mole) was distilled under vacuum with slow heating from 20° to 80° C. Benzene (40 ml) was added, followed by n-heptane (100 ml). The resulting mixture was stirred and a solution of diphenylsulfoxide 10.1 g, (0.050 mol), in benzene (60 ml) was added during 1 hour at 80° C. The mixture was stirred for 3 hours and cooled to room temperature. An 25% aqueous hydrobromic acid solution (180 ml) was slowly added to the reaction mixture (exotherm-). The layers were separated and the organic layer was extracted twice with 5% aqueous hydrobromic acid (2 x 30 ml). The combined aqueous extracts were extracted three times with dichloromethane (3 x 250 ml). The dichloromethane extracts were dried over magnesium sulfate, filtered and the organic solvent evaporated to leave triphenylsulfonium bromide (10.0 g, 59%).

1. temperaturewith slow heating from 20° to 80° C
2. stirringThe mixture was stirred for 3 hours
3. customThe layers were separated
4. extractionthe organic layer was extracted twice with 5% aqueous hydrobromic acid (2 x 30 ml)
5. extractionThe combined aqueous extracts were extracted three times with dichloromethane (3 x 250 ml)
6. dry with materialThe dichloromethane extracts were dried over magnesium sulfate
7. filtrationfiltered
8. customthe organic solvent evaporated

ORD record

ord-d7e07241cbfd4bea91c15ba101b8fb8e

Source dataset

uspto-grants-1990_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04980492