Water → 1-(1-(4-(Benzyloxy)phenyl)vinyl)-2-fluorobenzene

Participants

Reaction Conditions

Reaction Steps

Compound 1 (4.0 g, 13.1 mmol) was dissolved in dry THF (40 mL) and the solution was cooled to 0° C. CH3MgBr (15 mL, 19.5 mmol, 1.3 M) was added drop-wise. The resulting mixture was stirred at room temperature overnight. The solution was cooled to 0° C. and H2SO4 (2 mL, 98%) was added. A precipitate was formed and the inhomogeneous mixture was stirred at room temperature for 1 h. H2O (20 mL) was added and the mixture was extracted with diethyl ether (2×100 mL). The organic phase was washed with NaHCO3 (2×50 mL, saturated aqueous solution) and brine (50 mL) and dried over Na2SO4. Filtration and evaporation of the solvent under reduced pressure gave a crude material which was purified by column chromatography (heptane:ethyl acetate 6:1). Yield 2.58 g, 65% as an off-white solid. 1H-NMR (CDCl3) δ; 7.46-7.36 (m, 4H), 7.36 (m, 5H), 7.18-7.03 (m, 2H), 6.93 (d, 2H, J=8.6 Hz), 5.68 (d, 1H, J=1.0 Hz), 5.32 (s, 1H), 5.07 (s, 2H); 13C-NMR (CDCl3) δ 160.1 (d, J=248 Hz), 158.6, 143.5, 137.0, 133.4, 131.5 (d, J=3.5 Hz), 129.2 (d, J=8.1 Hz), 128.6 (2C), 128.0 (4C), 127.5 (2C), 123.9 (d, J=3.8 Hz), 115.7 (d, J=22.3 Hz), 115.3 (d, J=1.9 Hz), 114.6 (2C), 70.0.

Provenance & Evidence