Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sodium hydride (60% dispersion; 55 mg, 1.38 mmol) was added to a mixture of 4-benzyloxy-3-fluoro-phenol (Bionet Research, Camelford, Cornwall, UK; 250 mg, 1.15 mmol) in dimethylformamide (4 mL). After stirring for 15 min, iodoethane (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 215 mg, 1.38 mmol) was added and the reaction mixture was stirred overnight. Saturated sodium chloride was added to quench the reaction and the aqueous layer was extracted three times with ethyl acetate. The combined organic extracts were washed with saturated ammonium chloride and saturated sodium carbonate, and then dried over sodium sulfate. The mixture was filtered, concentrated and purified by flash chromatography on silica gel, eluting with 5% ethyl acetate/hexane to give 1-benzyloxy-4-ethoxy-2-fluoro-benzene (270 mg, 96%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.26 (t, 3H, J=7.0 Hz), 3.93 (q, 2H, J=7.0 Hz), 5.07 (s, 2H), 6.62-6.67 (m, 1H), 6.82-6.87 (m, 1H), 7.11 (t, 1H, J=9.0 Hz), 7.31-7.42 (m, 5H).
the reaction mixture was stirred overnight
to quench
the reaction
the aqueous layer was extracted three times with ethyl acetate
The combined organic extracts were washed with saturated ammonium chloride and saturated sodium carbonate
dried over sodium sulfate
The mixture was filtered
concentrated
purified by flash chromatography on silica gel
eluting with 5% ethyl acetate/hexane
Source ID: ord-bc1fdaa8e45d47779d544bfac5ace69e