Isopropyl iodide → 4-Bromo-2-ethyl-1-isopropoxybenzene

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (3.1 g, 22.4 mmol) followed by 2-iodopropane (0.75 mL, 7.5 mmol) were added to a solution of 4-bromo-2-ethyl-phenol (1.5 g, 7.5 mmol) in DMF (10 mL). The mixture was heated at 60° C. for 20 hours and then partitioned between 1N HCl and EtOAc. The organic layers were washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude yellow oil was purified by flash column chromatography (hexanes) to give the desired product (1.35 g, 75%). 1H NMR (400 MHz, CDCl3): δ 1.16 (t, J=7.6 Hz, 3 H), 1.32 (d, J=6.1 Hz, 6 H), 2.58 (q, J=7.6 Hz, 2 H), 4.49 (m, 1 H), 6.70 (d, J=8.6 Hz, 1 H), 7.23 (m, 2 H).

Provenance & Evidence