Methyl 2-(3-broMophenyl)-2-Methylpropanoate

150529-73-0

74-88-4

251458-15-8

Sodium hydride (60% oil solution, 10.4 g, 436 mmol) was added to tetrahydrofuran (400 mL) under argon protection, stirred and heated to 50 °C. Subsequently, methyl 2-(3-bromophenyl)acetate (20 g, 87.3 mmol) was added. The reaction mixture was added dropwise over 30 minutes and continued to be heated at 50 °C for 90 minutes. After completion of the reaction, the temperature was lowered to below 40 °C and iodomethane (13 mL, 209 mmol) was added over 10 min. The resulting suspension was stirred overnight at room temperature. At the end of the reaction, water (300 mL) was carefully added and the reaction mixture was concentrated. The residue was partitioned between ether (400 mL) and water. The aqueous layer was extracted with ether (400 mL) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated to give the crude product. The crude product was purified by column chromatography using a gradient elution with a heptane solution of 0 to 20% ethyl acetate to afford methyl 2-(3-bromophenyl)-2-methylpropionate (14.96 g, 58 mmol, 67% yield).1H NMR (400 MHz, CDCl3): δ 7.47 (t, 1H), 7.37 (dt, 1H), 7.24 (dt. 1H), 7.18 (t, 1H), 3.65 (s, 3H), 1.55 (s, 6H).