Hydrochloric Acid → 2-(2,5-Difluorophenyl)-6-(4-ethoxy-2-nitrophenoxy)chroman

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320 mg of 2-(2,5-Difluorophenyl)chroman-6-ol (Example 14(c)) was dissolved in dry DMF and potassium tert-butoxide (150 mg) was added. The resulting mixture was stirred for 30 minutes and 1-chloro-4-ethoxy-2-nitrobenzene (250 mg) was added. The reaction mixture was refluxed for 8 hours. After cooling to room temperature 1 M HCl-solution was added into the reaction mixture and it was extracted with ethyl acetate. The combined organic extracts were washed with water and saturated NaCl-solution. The product was purified by column chromatography using heptane-ethyl acetate (3:1) as an eluant. 1H NMR (300 MHz, CDCl3) δ: 7.43 (d, 1H, J 2.9Hz), 7.25 (m, 1H), 7.08-6.97 (m, 4H), 6.89-6.75 (m, 3H), 5.31 (d, 1H, J 9.1 Hz), 4.06 (q, 2H, J 7.0 Hz), 2.97 (m, 1H), 2.74 (m, 1H), 2.26 (m, 1H), 1.98 (m, 1H), 1.44 (t, 3H, 7.0 Hz).

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