Acetone → Methyl 3-fluoro-2-methoxybenzoate

Participants

Reaction Steps

A mixture containing 3-fluorosalicylic acid (20 g) [obtained as white crystals, m.p. 145°-147° C., by the method of L N Ferguson et alia, J.Amer.Chem.Soc., 1950, 72, 5315], iodomethane (60 g), potassium carbonate (40 g) and acetone (200 ml) was heated under reflux for 24 hours. Water (500 ml) was added and the mixture was extracted with ether (3×150 ml). The combined extracts were dried (MgSO4) and evaporated to give methyl 3-fluoro-2-methoxybenzoate (B) (21 g) as a yellow oil, which was used without further purification; NMR: 3.85 (3H,s), 3.95 (3H,s) and 6.8-7.6 (3H,m).

Provenance & Evidence