Hydrochloric Acid → 3,5-Difluoro-4'-hydroxystilbene

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Reaction Steps

To a solution of 3,5-difluoro-4′-acetoxystilbene (0.69 g, 2.5 mmol) in MeOH (10 ml) was added 5 mL 4M HCl in 1,4-dioxane. The mixture was stirred for 20 minutes at ambient temperature. After purification by flash column, 3,5-difluoro-4′-hydroxystilbene (0.51 g, 88%) was obtained. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.40 (m, 2H), 7.05-6.83 (m, 6H), 6.67 (tt, 1H), 4.88 (s, 1H); 13C NMR (CDCl3, 75 MHz) δ 164.49(d), 162.47, 156.01, 141.29, 130.90, 128.53, 124.74, 115.96, 109.03 (t), 102.53 (t); 19F NMR (CDCl3, 282 MHz) δ-31278.95 (t, J=1720.2 Hz); HRMS (EI+) found 232.0715 M+, calcd 232.0700 for C14H10F2O.

Provenance & Evidence