Methyl iodide → 2-Bromo-5-methoxy-1,3-dimethylbenzene

Participants

Reaction Steps

A mixture of commercially available 4-bromo-3,5-dimethylphenol (a compound of Formula 4) (25.0 g, 124.3 mmol), methyl iodide (35.3 g, 248.6 mmol), and potassium carbonate (34.4 g, 248.6 mmol) in 62.5 mL of DMF was stirred for 2 hours at room temperature. The reaction mixture was diluted with 300 mL of ether and washed with 250 mL of water and 5×100 mL of brine. The organic portion was dried (MgSO4), filtered, and evaporated to give an oil, which was purified by flash column chromatography (silica gel, 90:10 hexane/ethylacetate) to give 4-bromo-3,5-dimethylanisole (a compound of Formula 5) (26 g, 120.8 mmol, 97%); 1HNMR (CDCl3) δ2.39 (s, 6H), 3.76 (s, 3H), 6.67 (s, 2H).

Provenance & Evidence