Methyl iodide → HCID 67243804, compound

Participants

Reaction Steps

To a solution of 2-ethoxy-4-(2-hydroxy-1,1-dimethylethyl)iodobenzene (1.0 g, 3.123 mmol, example 4) in tetrahydrofuran cooled to 0° C. was added sodium hydride (150 mg, 6.246 mmol, 60% in mineral oil). Iodomethane (0.58 mL, 9.369 mmol) was added after 15 min. The icebath was then removed and the reaction mixture was stirred at room temperature for 12 h. Saturated solution of ammonium chloride was added and the mixture was partitioned between ethyl acetate (20 mL) and water (5 mL). The product was extracted with ethyl acetate (2×). The organic layers were washed with water (1×), brine (1×), dried over anhydrous sodium sulfate and concentrated. Purification of the crude residue by flash column chromatography (silica gel, eluting with a gradient of 0-60% ethyl acetate in hexanes) gave 2-ethoxy-4-(2-methoxy-1,1-dimethylethyl)iodobenzene (891 mg, 85% yield) as clear oil.

Provenance & Evidence