ChemicalBook CAS DataBase List Triphenylsulfonium Bromide

Triphenylsulfonium Bromide synthesis

5synthesis methods

Product Name:Triphenylsulfonium Bromide
CAS Number:3353-89-7
Molecular formula:C18H15BrS
Molecular Weight:343.28

Triphenylsulfonium bromide synthesis: 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 (300 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 (3×250 ml). The dichloromethane extracts were dried over magnesium sulfate, filtered and the organic solvent evaporated to leave triphenylsulfonium bromide (10.2 g, 60%), which was crystallized from dichloromethane/diethyl ether. M.p. 285-7°C.

106-38-7
401 suppliers
$14.00/5g

945-51-7 Synthesis

945-51-7
253 suppliers
$5.00/5g

3353-89-7
57 suppliers
$40.00/100mg

Sulfonium, (4-methylphenyl)diphenyl-, bromide

4189-82-6
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Yield:4189-82-6 72% ，3353-89-7 1%

Reaction Conditions:

Stage #1: para-bromotoluene;1,1'-sulfinylbisbenzenewith chloro-trimethyl-silane;magnesium in tetrahydrofuran at -5 - 20; for 0.5 h;
Stage #2: with hydrogen bromide in tetrahydrofuran;water;Product distribution / selectivity;

Steps:

2

Comparative Example 1 and Experimental Examples 1 to 6. Effect of the equivalent of an activator relating to the present invention The same procedure as in Example 1 was carried out except for using TMSCl (5 equiv.) used in Example 1 in the various equivalents shown in the following Table 5, to obtain objective 4-methylphenyldiphenylsulfonium bromide. Yields of the obtained objective compound, triphenylsulfonium bromide (byproduct 1) and bis(4-methylphenyl)phenyl sulfonium bromide (byproduct 2) are shown in Table 5.

References:

EP1676835,2006,A1 Location in patent:Page/Page column 21-22

108-86-1 Synthesis