A mixture of 2.0 g of α-(chloromethyl)-4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-methanol, 4.0 g of 2,6-difluorobenzonitrile, and 15 mL of dichloromethane was cooled to 5° C. and 0.8 mL of conc. sulfuric acid was added dropwise over 7 min. After 30 min, ice was added, the mixture was diluted with hexanes, and the crude product was filtered and dried to afford 1.0 g of product, m.p. 144-145° C. 1H-NMR (CDCl3): δ4.0 (dq, 2), 5.6 (m, 1H), 6.75 (br d, 1H), 6.85 (t, 1H, J=60 Hz), 7.0 (t, 2H), 7.4 (m, 1H), 7.5 (d, 2H), 7.6 (m, 6H). The filtrate was extracted with ethyl acetate; the extract was washed with water, concentrated, and chromatographed on silica gel to afford an additional 0.5 g of product, corresponding to a total yield of 52%.
