Potassium Carbonate → 2-Bromo-4-ethyl-1-(2-methoxy-ethoxy)-benzene

Participants

Reaction Steps

Potassium carbonate (8.25 g, 60 mol) followed by 2-bromoethyl methyl ether (1.87 mL, 20 mmol) were added to a solution of 2-bromo-4-ethyl-phenol (4 g, 20 mmol, from step 1 of Example B(98)) in DMF (25 mL). The mixture was stirred for 20 hours and then partitioned between 1N HCl and EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated. The crude yellow oil was purified by flash column chromatography (0% to 10% EtOAc in hexanes) to give the desired product (4.63 g, 90%). 1H NMR (400 MHz, CDCl3): δ 1.20 (t, J=7.6 Hz, 3 H), 2.57 (q, J=7.6 Hz, 2 H), 3.48 (s, 3 H), 3.79 (t, J=5.1 Hz, 2 H), 4.15 (t, J=4.8 Hz, 2 H), 6.85 (d, J=8.3 Hz, 1 H), 7.06 (dd, J=8.3, 2.3 Hz, 1 H), 7.37 (d, J=2.3 Hz, 1 H).

Provenance & Evidence