[F:1][C:2]1[CH:3]=[CH:4][C:5]([SH:11])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.Br[CH2:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:13]([C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[C:8]([CH3:9])[C:6]=2[CH:7]=1To a solution of 5.20 g 1-(5-fluoro-2-mercaptophenyl)ethanone in 100 mL anhydrous DMF was added 5.47 g 1-bromopinacolone and 10.95 g cesium carbonate. The resulting mixture was stirred at room temperature overnight and then heated at 70° C. for 3 days. After diluting the reaction mixture with ice and water, it was extracted with ether several times. The combined ether extract was washed with 0.05 N NaOH (2×), water (3×), and saturated brine, dried over anhydrous Na2SO4, and evaporated to give the crude product. The latter was purified by SGC using 10˜15% EtOAc in hexanes to give the title compound as an oil. 1H NMR (CDCl3, 500 MHz) 7.77 (dd, JH-H=8.7 Hz, JH-F=4.8 Hz, 1H), 7.49 (dd, JH-H=2.5 Hz, JH-F=9.6 Hz, 1H), 7.24 (ddd, JH-H=2.5 & 8.7 Hz, JH-F=8.7 Hz, 1H), 2.53 (s, 3H), 1.40 (s, 9H). LC-MS: 4.11 min. (m/Z=209.1, 251.1).
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