Jan.  13, 2011  91  US 2011/0008728 Al  was collected, and washed once with 150 g of a 10% aqueous  solution of sodium chloride and once with pure water. Then,  the organic phase was concentrated and solidified, thereby  obtaining 20.9 g of a compound (8) in the form of a white  solid (Br:Cl=15.4:84.6).  [Chemical Formula 116]  [1171]  The obtained acid generator (B14) was analyzed by  $^{1}$H-NMR and $^{19}$F-NMR. $^{1}$H-NMR (DMSO-d6, 400 MHz):  Ii  (ppm)=0.87 (t, 3H,  Ha),  1.29 (m, 4H, He, Hd), 1 .45 (m, 2H,  Hd), 1.65-1.95 (m, 17H, He, Hk), 2.33 (s, 6H, Hg), 3.83 (t,  2H, Hf), 4.54 (t, 2H, Hj), 7.59 (s, 2H, Hh), 7.73-7.85 (m, l0H,  Hi)  [1172]  $^{19}$F-NMR (DMSO-d6, 400 MHz):  Ii  (ppm)=-111.5  ( t, 2F, Fa) (potassium nonafluoro-n-butanesulfonate was used  as an internal standard, and the peak of hexafluorobenzene  was regarded as -160 ppm.)  [1173]  From the results shown above, it was confirmed that  the acid generator (B14) had a structure shown below. Fur› thermore, from the results of $^{19}$F-NMR analysis, it was con› firmed that the purity was 99.7 wt%.  [Chemical Formula 115]  [1174]  (i) Synthesis of Compound (8)  [1175]  21.7 g of a compound (6) (Br:Cl=85.2:14.2) was  dissolved in 108.5 g of acetonitrile, and 6.00 g of triethy› lamine was further added to obtain a uniform solution. Then,  57 .6 g of a 25 wt % acetonitrile solution of a compound (7)  was dropwise added thereto, and a reaction was effected at a  reflux temperature for 2 hours. Subsequently, acetonitrile was  removed, and the resultant was dissolved in 300 g of pure  water, followed by washing twice with 150 g of a mixed  solvent containing n-hexane and TBME (1: 1 wt/wt).  [1176]  Thereafter, 300 g of methylene chloride and 30 g of  sodium chloride were added and stirred. The organic phase  [1177]  (ii) Synthesis of Acid Generator (B 15)  [1178]  5.00 g of the compound (8) (Br:Cl=15.4:84.6) was  mixed with 3 .25 g ofa compound (2), and 50.0 g of pure water  and 50.0 g of methylene chloride were added thereto, fol› lowed by stirring at room temperature for 4 hours. Thereafter,  the organic phase was collected, and washing was conducted  twice with 25.0 g of a 1 % aqueous hydrochloric acid solution  and 4 times with 25 .0 g of pure water. Then, the organic phase  was concentrated and solidified, thereby obtaining 5.00 g of  an acid generator (B 15) in the form of a white solid.  Acid-Generator Synthesis Example 6  Synthesis of Acid Generator (B 15)  Compound (6)  0 0  +  Br/Cl  Compound (7)  -- 0 0  Br/Cl  Compound (8)  Acid generator (B14) 