Methyl iodide → 4-(2,6-Dichloro-4-methoxymethyl-phenoxy)-anisole

Participants

Reaction Steps

To a solution of the title compound of Step A (400 mg, 1.34 mmol) in dry dimethylformamide (13 mL) at 0° C. under nitrogen was added NaH (60% dispersion in mineral oil, 134 mg, 3.3 mmol). After stirring for 30 minutes at 0° C. until hydrogen evolution ceased, methyl iodide (949 mg, 6.61 mmol) was added. The reaction mixture was warmed to room temperature and stirred for about 19 hours. The solution was poured into water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with 1M HCl (3×100 ml), brine (100 ml), dried, filtered, and concentrated. The crude product was purified by preparative TLC (30% hexane in dichloromethane) to afford the title compound (410 mg). NMR (400 MHz, CDCl3) δ7.36 (s, 2H), 6.75-6.83 (m, 4H), 4.40 (s, 2H), 3.75 (s, 3H), 3.43 (s, 3H).

Provenance & Evidence