Water → HCID 53304460, compound

Participants

Reaction Conditions

Reaction Steps

Nitrogen was bubbled through a mixture of 2-bromo-4-fluorophenol (1.6 g, 8.38 mmol), vinylboronic anhydride pyridine complex (95%, 806 mg, 3.35 mol) and potassium carbonate (1.17 g, 8.38 mmol) in 1,2-dimethoxyethane (15 mL) for 30 minutes. To this mixture was added palladium tetrakis(triphenylphosphine) (97.2 mg, 0.084 mmol). The reaction was allowed to stir at 90° C. for 16 hours. Water (50 mL) was added, and the mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with aqueous sodium hydroxide solution (1 N, 100 mL) and saturated aqueous sodium chloride solution (100 mL), dried over magnesium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 30% ethyl acetate in heptanes) afforded the title compound as a white solid. Yield: 1.03 g, 7.46 mmol, 89%. 1H NMR (400 MHz, CDCl3) δ 4.91 (br s, 1H), 5.41 (dd, J=11.1, 1.0 Hz, 1H), 5.74 (dd, J=17.6, 1.0 Hz, 1H), 6.74 (dd, J=8.8, 4.7 Hz, 1H), 6.82-6.95 (m, 2H), 7.10 (dd, J=9.5, 3.0 Hz, 1H).

Provenance & Evidence