Methanol → Methyl 2-fluoro-5-methylbenzoate

Participants

Reaction Steps

To a solution of 2-fluoro-5-methylbenzoic acid (20.0 g, 0.13 mol) in MeOH (100 mL) is added thionyl chloride (1.9 mL, 26.0 mmol) dropwise, via syringe, and the solution is refluxed overnight. After cooling, the solvent is evaporated, and the residue is taken up in ethyl acetate (200 mL), extracted with sat'd aq. NaHCO3 (50 mL), brine (50 mL), water (50 mL), dried (MgSO4), and chromatographed (silica, 5% EtOAc/hexane) to yield methyl 2-fluoro-5-methylbenzoate, as a clear oil.

Provenance & Evidence