N1C=CN=C1.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]([OH:16])[CH2:14][OH:15])=[CH:9][C:8]=1[F:17].[CH3:18][C:19]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C(Cl)Cl>[Si:22]([O:15][CH2:14][C@@H:13]([C:10]1[CH:11]=[CH:12][C:7]([Cl:6])=[C:8]([F:17])[CH:9]=1)[OH:16])([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23]Imidazole (13.1 g, 193 mmol) was added to a cold (0° C.) solution of (R)-1-(4-chloro-3-fluorophenyl)ethane-1,2-diol (14.7 g, 77.1 mmol) in DCM (100 mL), followed by TBSCl (12.8 g, 84.8 mmol). The reaction mixture was stirred at 0° C. for 1 hour and then quenched with water (50 mL). The layers were separated, and the organics were dried, filtered and concentrated. The crude product was purified via column chromatography, eluting with hexanes/ethyl acetate (100:1) to give (R)-2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanol (11.0 g, 47% over two steps). 1H NMR (400 MHz, CDCl3) δ 7.36 (m, 1H), 7.20 (m, 1H), 7.08 (m, 1H), 4.71 (m, 1H), 3.75 (m, 1H), 3.49 (m, 1H), 2.96 (d, J=2.6 Hz, 1H), 0.90 (s, 9H), 0.07 (s, 3H), 0.06 (s, 3H).
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