Methanol → Methyl 2-(4-fluorophenyl)acetate

Participants

Reaction Steps

4-Fluorophenyl acetic acid (25 g) was dissolved in anhydrous methanol, stirred under nitrogen and cooled in an ice/methanol bath. Dry HCl gas was bubbled through the reaction for 1 hr. The methanol was removed by rotary evaporator and the residue was dispersed between aqueous sodium hydrogen carbonate and dichloromethane. The organic layer was washed with brine, dried (MgSO4) and concentrated to afford the title compound as a clear oil (24.4 g). 1H NMR (360 MHz, CDCl3) δ 3.61 (2H, s), 3.70 (3H, s), 6.97-7.06 (2H, m), 7.20-7.27 (2H, m). MS Cl+ 169 [M+H]+.

Provenance & Evidence