183  US 9,958,775 B2  184  $^{19}$H-NMR (CDC1$_{3}$ :  ppm)  Ii:  -118.710 (2F, t, J=15.2 Hz),  -113.968 (2F, t, J=15.2 Hz), -108.393 (2F, t, J=15.2 Hz).  10 g of A-le was dissolved in 100 mL of methanol, 7.7 g  5  of triphenylsulfonium bromide was added thereto, and the  mixture was stirred at room temperature. After the reaction  ends, the obtained reaction solution was condensed under  reduced pressure and 100 mL of ethyl acetate and 100 mL  of distilled water were added thereto. Next, the obtained 10  solution was moved to a separating funnel and the aqueous  layer was removed. Thereafter, the organic layer was  washed with 200 mL of distilled water for three times, and  then the organic layer was condensed. After the concentrate  was purified by using a silica gel colunm chromatography  15  ( eluent: methanol) and a solvent was distilled off at reduced  pressure, 8 g of a compound (A-1) was obtained by per› forming vacuum drying.  $^{1}$H-NMR (CDC1$_{3}$ :  ppm)  Ii:  1.33 (9H, s), 3.39 (6H, s), 4.58  (4H, s), 7.49 (2H, s), 7.73 (15H, m)  $^{19}$H-NMR (CDC1$_{3}$ :  ppm)  Ii:  -118.314 (2F, t, J=15.2 Hz),  -114.020 (2F, t, J=15.2 Hz), -107.933 (2F, t, J=15.2 Hz).  After 10 g of a compoundA-l0a was dissolved in 200 mL  of methanol and 8.5 g of triphenylsulfonium bromide was  added thereto, and the mixture was stirred for 4 hours at  room temperature. After 200 mL of ethyl acetate and 200 mL  of distilled water were added to the obtained reaction  solution, the obtained solution was moved to a separating  funnel and the aqueous layer was removed. Thereafter, the  organic layer was washed with 200 mL of distilled water for  three times, and then a solvent of the organic layer was  distilled off at reduced pressure to obtain 13.5 g of a  compound (A-10).  After 10 g of a compound A-6a was dissolved in 200 mL  of methanol and 6.1 g of triphenylsulfonium bromide was  added thereto, and the mixture was stirred for 4 hours at  room temperature. After 200 mL of ethyl acetate and 200 mL  of distilled water were added to the obtained reaction  solution, the obtained solution was moved to a separating  funnel and the aqueous layer was removed. Thereafter, the  organic layer was washed with 200 mL of distilled water for  three times, and then a solvent of the organic layer was  distilled off at reduced pressure to obtain 17.7 g of a  compound (A-6). $^{1}$H-NMR (CDC1$_{3}$ :  ppm)  Ii:  3.36 (3H, s),  3.38 (3H, s), 3.42 (3H, s), 3.86 (3H, s), 4.51 (2H, s), 4.56  (4H, s), 7.63 (lH, s), 7.79-7.66 (15H, m).  Synthesis Example 3: Synthesis of Compound  (A-10)  (Synthesis of A-1)  Synthesis Example 2: Synthesis of Compound  (A-6)  0- -o-1-F+-1--+l-----<lt--1-o  -- 0  F F F 0  A-6a  0  II  -o-s  II  0  0- O› F F F  0  I I I ~- 0  F F F O  0  o› A-6  [Chem. 103]  Synthesis Example 4: Synthesis of Compound  (A-13)  Na+  \  0  F  0  -03S+~-O  II  F  0  0  I  A-13a  [Chem. 105]  [Chem. 104]  -o-1-F+-1--+l-l>--1-o  -- 0  F F F 0  A-l0a  Q  0  F F F  -o-~  I I I  0  F F F  i-o~O-:;  II  - 0  O-CF3  A-10 