2-(3-trifluoromethylphenyl)propionic acid

Synthesis

A solution of 3-(trifluoromethyl)phenylacetic acid (ALDRICH, 300 mg, 1 .470 mmol) in THF (2 mL) was added dropwise to a solution of lithium diisopropylamide, 2M solution in heptane/THF/ethylbenzene (ALDRICH, 2.94 mL, 5.88 mmol) in THF (5 mL) at -78 °C. After 1 h at -78 °C, methyl iodide (ALDRICH, 0.735 mL, 1 1.76 mmol) was added, and the solution was stirred for 1 hour. The mixture was hydrolyzed with 2N HCI until acidic pH was reached, extracted with DCM, dried over MgS04, filtered, and dried under vacuum to produce a crude. It was purified by flash column chromatography using hexane/EtOAc 85/15 to 0/100 to give 2-(3-trifluoromethylphenyl)propionic acid (304 mg, 1.39 mmol, 95% yield).