US 8,962,233 B2  135  136  (11) Synthesis of Compound Al-38  CompoundAl-38 amounting to 19.4 gwas obtained in the  same manner as in the synthesis of compound Al-35 except  that 10.0 g of sulfonium salt A was changed to 10.0 g of  below-shown sulfonium salt B.  (6) Synthesis ofCompoundAl-16  CompoundAl-16 amounting to 20.8 g was obtained in the  same manner as in the synthesis of compound Al-12 except  that 11.4 g of diphenyl sulfoxide was changed to 10.0 g of  dibenzothiopheneoxide.  (7) Synthesis ofCompoundAl-19  CompoundAl-19 amounting to 19.5 gwas obtained in the  same manner as in the synthesis of compound Al-12 except  that 11.4 g of diphenyl sulfoxide was changed to 10.0 g of  phenoxathiinoxide.  (8) Synthesis ofCompoundAl-24  CompoundAl-24 amounting to 7.5 g was obtained in the  same manner as in the synthesis of compound Al-1 except  that 40.0 g of sodium 2,4,6-tricyclohexylbenzenesulfonate  was changed to 5.0 g of sodium 2,4,6-triisopropylbenzene› sulfonate.  (9) Synthesis ofCompoundAl-31  CompoundAl-31 amounting to 7.5 g was obtained in the  same manner as in the synthesis of compound Al-1 except  that 40.0 g of sodium 2,4,6-tricyclohexylbenzenesulfonate  was changed to 5.0 g of sodium 2,4,6-tritert-butylbenzene› sulfonate.  (10) Synthesis of Compound Al-35  First, 20.0 g of 2,4,6-tricyclohexylbromobenzene was dis- solved in 800 ml of diethyl ether. In a nitrogen atmosphere,  6.0 g oftetramethylethylenediamine and 31.9 ml ofn-butyl› lithium (1.63M hexane solution) were added to the solution at  0°  C., and agitated at 0°  C. for an hour. The resultant reaction  solution was dropped into a solution obtained by dissolving  15.7 g of 1,1,2,2,3,3-hexafluoropropane-l,3-disulfonyl dif› luoride in 200 ml of diethyl ether at 0°  C. over a period of30  minutes. After the completion of dropping, the mixture was  further agitated for 30 minutes, and 200 ml of distilled water  was added thereto. The thus obtained organic phase was  washed with saturated saline twice. The solvent was removed,  and 100 ml of methanol and 100 ml of IN aqueous sodium  hydroxide solution were added to the residue and agitated for  an hour. Methanol was distilled off, and ethyl acetate was  added to the residue. The thus obtained organic phase was  washed with saturated saline twice. The solvent was distilled  off, and the thus obtained solid was washed with hexane. The  resultant solid was dissolved in 100 ml of methanol, and 10.0  g ofbelow-shown sulfonium salt A was added to the solution  and agitated for two hours. The solvent was distilled off, and  ethyl acetate was added to the residue. The thus obtained  organic phase was sequentially washed with a saturated aque› ous sodium hydrogen carbonate solution and water. The sol› vent was distilled off, thereby obtaining 23.5 g of desired  white solid compound (Al-35).  CompoundAl-64 amounting to 12.8 g was obtained in the  same manner as in the synthesis of compound Al-35 except  that 20.0 g of2,4,6-tricyclohexylbromobenzene was changed  to 10.0 g ofpiperidine and that 10.0 g ofsulfonium saltA was  changed to 10.0 g of below-shown sulfonium salt C.  (14) Synthesis ofcompoundAl-64  First, 20.0 g of 2,4,6-tricyclohexylbromobenzene was dis› solved in 800 ml of diethyl ether. In a nitrogen atmosphere,  6.0 g oftetramethylethylenediamine and 31.9 ml ofn-butyl› lithium (1.63M hexane solution) were added to the solution at  0°  C., and agitated at 0°  C. for an hour. The resultant reaction  solution was dropped into a solution obtained by dissolving  15.7 g of 1,1,2,2,3,3-hexafluoropropane-l,3-disulfonyl dif- luoride in 200 ml of diethyl ether at 0°  C. over a period of30  minutes. After the completion of dropping, the mixture was  further agitated for 30 minutes, and 10 ml of triethylamine  and 4.50 g of trifluorosulfonamide were added thereto. The  mixture was agitated at 0° C. for an hour, and 200 ml of  distilled water was added thereto. The thus obtained organic  phase was washed with saturated saline twice. The solvent  was removed, and 100 ml of methanol and 100 ml of IN  aqueous sodium hydroxide solution were added to the residue  and agitated for an hour. Methanol was distilled off, and ethyl  acetate was added to the residue. The thus obtained organic  phase was washed with saturated saline twice. The solvent  was distilled off, and the thus obtained solid was washed with  hexane. The resultant solid was dissolved in 100 ml of metha- no!, and 10.0 g of sodium 2,4,6-tricyclohexylbenzene› sulfonate was added to the solution and agitated for two  hours. The solvent was distilled off, and ethyl acetate was  added to the residue. The thus obtained organic phase was  sequentially washed with a saturated aqueous sodium hydro- gen carbonate solution and water. The solvent was distilled  off, thereby obtaining 21.2 g of desired white solid compound  (Al-54).  (13) Synthesis ofCompoundAl-54  CompoundAl-50 amounting to 14.8 g was obtained in the  same manner as in the synthesis of compound Al-35 except  that 20.0 g of2,4,6-tricyclohexylbromobenzene was changed  to 20.0 g of 2,4,6-triisopropylbromobenzene.  (12) Synthesis ofCompoundAl-50  (B)  (A)