Ammonium Chloride → 1-(4-(5-Benzylbenzofuran-2-yl)-3-fluorophenyl)ethanol

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-(5-benzylbenzofuran-2-yl)-3-fluorobenzaldehyde (0.559 g, 2 mmol) in THF at 0° C. was added methyl-magnesium bromide (1.4M solution in toluene/THF=3:1, 2.40 mL, 3 mmol) dropwise over 5 min. The mixture was allowed to stir for 20 min at 0° C., treated with NH4Cl, extracted with EtOAc, dried over MgSO4, and evaporated. The crude product was purified by flash chromatography (EtOAc/hexanes) to give 1-(4-(5-benzylbenzofuran-2-yl)-3-fluorophenyl)ethanol. 1H NMR (300 MHz, CDCl3) δ ppm 7.98 (t, J=8.0 Hz, 1H), 7.38-7.46 (m, 2H), 7.10-7.34 (m, 9H), 4.77-5.04 (m, 1H), 4.08 (s, 2H), 1.85 (d, J=3.8 Hz, 1H), 1.46-1.60 (m, 3H). MS (ESI) m/z: Calculated; 346.1 Observed: 347.1 (M++1).

Provenance & Evidence