Ammonium Chloride → 4-[1,3]Dioxolan-2-yl-2-fluorophenol

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Reaktionsschritte

A solution of 2-(3-Fluoro-4-methoxy-phenyl)-[1,3]-dioxolane (250 mg, 1.26 mmol) and Sodium thiomethoxide (106 mg, 1.51 mmol) in dry N,N-dimethylformamide (3.5 mL) was heated at 100° C. under nitrogen for 4 hours. Then a saturated solution of ammonium chloride (15 mL) was added and the aqueous layer extracted with methylene chloride (4×10 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under vacuum. The residue was chromatographed (silica gel, hexanes/ethyl acetate 7:3) to produce 4-[1,3]dioxolan-2-yl-2-fluoro-phenol as a pale brown oil (120 mg, 52%). 1H-NMR (CDCl3, 200.15 MHz): δ 7.24–7.01 (m, 2H), 6.88 (t, 1H, J=8.4), 6.07 (sa, 1H), 5.71 (s, 1H), 4.13–3.95 (m, 4H).

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