106  US 8,691,490 B2  105  4-(2-methacryloyloxyethoxy)phenyldiphenylsulfonium  4-methylbenzenesulfonate of Synthesis Example 1-1 and tri› ethylanm10nium 1, 1,3,3,3-pentafluoro-2-(methacryloyloxy)  propane-1-sulfonate of Synthesis Example 1-2 are mixed and  ion-changed in a dichloromethane-water system. An organic  layer after washing by water was concentrated under reduced  pressure, the residue was purified by silica gel column chro› matograph, and thereby the intended substance was obtained  as an oily substance. The structure of the intended substance  is shown below.  Spectrum data of the intended substance thus obtained are  shown below. Results of the nuclear magnetic resonance  spectra (1H-NMR, $^{19}$F-NMR/DMSO-d$_{6}$) are showninFIG.1  and FIG.  2,  respectively. Meanwhile, trace amounts of  residual solvents ( diisopropyl ether and water) are detected in  $^{1}$H-NMR.  IR Spectrum (IR(KBr); cm- 1 ): 1743, 1717, 1590, 1496,  1477, 1448, 1372,1311, 1296,1264, 1215, 1169,1133, 1069,  994, 949, 902, 839, 750, 684 and 642 cm- 1  Time-of-Flight  Mass  Spectrum Analysis  (TOFMS;  MARDI): POSITIVE: M+ $^{391 }$(corresponding to C$_{24}$H$_{23}$ 0$_{3}$ S)  NEGATIVE: M- 297 ( corresponding to C$_{7}$H$_{6}$F  $_{5}$0 $_{5}$S)  4-hydroxyphenyldiphenylsulfonium  4-methylbenzene› sulfonate and triethylammonium 1,1,3,3,3-pentafluoro-2- (methacryloyloxy)propane-l-sulfonate  of  Synthesis  Example 1-2 are mixed and ion-changed in a dichlo› romethane-water system. An organic layer after washing by 65  water was concentrated under reduced pressure and was used  for the next reaction as a crude substance.  After 20 mmoles of 4-hydroxyphenyldiphenylsulfonium  1, 1,3 ,3 ,3-pentafluoro-2-( methacry loy loxy )propane-1-sul› fonate obtained in Synthesis Example 1-4, 22 mmoles of  methacrylic acid anhydride, 24 mmoles oftriethylamine and  4 mmoles of N,N-dimethylaminopyridine were mixed and  stirred overnight, the reaction was terminated by adding  dilute hydrochloric acid to the reaction solution. Thereafter,  an organic layer of the quenched reaction solution was sepa› rated, and then washed by water, and dichloromethane was  removed by evaporation under reduced pressure. Methyl  isobutyl ketone was added into the residue, and an organic  layer was separated and then washed by water, and methyl  isobutyl ketone was removed by evaporation under reduced  pressure. The obtained residue was washed by diisopropyl  ether, and thereby the intended substance was obtained as an  oily substance (with yield of 76%). The structure of the  intended substance is shown below.  Synthesis Example 1-3  Synthesis of 4-(2-methacryloyloxyethoxy)phenyl› diphenylsulfonium 1, 1,3,3,3-pentafluoro-2-(meth› acryloyloxy )propane-l-sulfonate (PAG-1)  Synthesis Example 1-5  Synthesis of 4-methacryloyloxyphenyldiphe› nylsulfonium 1,1,3,3,3-pentafluoro-2-(methacryloy› loxy)propane-l-sulfonate (PAG-2)  Synthesis Example 1-4  Synthesis of 4-hydroxyphenyldiphenylsulfonium  1, 1,3 ,3 ,3-pentafluoro-2-( methacry loy loxy )propane- 1-sulfonate  Jl  . F F  (  /  ’(’C’s~  <  \ -continued 