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

Participants

Reaction Steps

A mixture of 4-bromo-3,5-dimethylphenol (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 (5) (26 g, 120.8 mmol, 97%); 1HNMR (CDCl3) δ 2.39 (s, 6H), 3.76 (s, 3H), 6.67 (s, 2H).

Provenance & Evidence