Methyl iodide → 2-(4-Fluorophenyl)propionic acid

Methyl (4-fluorophenyl)acetate (0.5 g) was dissolved in DMF (81 mL). The mixture was cooled in an ice bath and NaH (131 mg, 60% w/w in mineral oil) was added. The mixture was stirred for 1 h at RT and again cooled in an ice bath before the addition of MeI (633 mg). The mixture was warmed to RT and, the reaction was quenched with ½ (sat.) aqueous ammonium chloride. Work up consisted of extraction of the aqueous layer with ether (2×). The combined organic fractions were washed with water and brine, then dried (MgSO4). The solvent was evaporated under reduced pressure and methyl 2-(4-fluorophenyl)propanoate was purified on silica gel (ethyl acetate/hexanes). Methyl 2-(4-fluorophenyl)propanoate (420 mg) was dissolved in 12 mL THF and 6 mL MeOH. 6 mL of KOH (2M) was added and the mixture was stirred for 2 h at RT. Water was added and the organic solvents were removed. The base was quenched with icy hydrochloric acid (1N), DCM was added and the phases separated with a phase separator. The solvent was removed under reduced pressure to provide the title compound.