Methyl iodide → Methyl 2-(4-iodophenyl)propanoate

Participants

Reaction Conditions

Reaction Steps

A stirred, cooled (−78° C.) solution of methyl-4-iodophenyl acetate (described in U.S. Pat. No. 6,252,090, incorporated herein by reference; 2.77 g, 10 mmol) in anhydrous tetrahydrofuran (20 mL) was treated with a 1.5M solution of lithium diisopropyl amide in tetrahydrofuran and cyclohexane (8 mL, 12 mmol). The reaction mixture was allowed to warm to 0° C. over 40 minutes, cooled again to −78° C. and treated with methyl iodide (0.75 mL, 12 mmol). The reaction mixture was allowed to warm to room temperature over 1 h. It was then quenched with saturated aqueous ammonium chloride solution, diluted with water and extracted with diethyl ether. The combined organic phase was washed with brine (×1), dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a yellow oil (2.7 g, 92.7%).

Provenance & Evidence