2-Fluoro-6-nitrobenzoic acid methyl ester

385-02-4

18107-18-1

212189-78-1

General procedure for the synthesis of methyl 2-fluoro-6-nitrobenzoate from 2-fluoro-6-nitrobenzoic acid and trimethylsilylated diazomethane: 2-fluoro-6-nitrobenzoic acid (712 mg, 3.85 mmol) was dissolved in a mixed solvent of methanol/acetonitrile (10 mL/10 mL) under nitrogen protection and cooled to 0 °C. Trimethylsilylated diazomethane solution was slowly added dropwise until the reaction solution took on a persistent yellow color, and stirring was continued at 0 °C for 30 min. Subsequently, the reaction was quenched with glacial acetic acid until the yellow color disappeared. The solvent was partially evaporated under reduced pressure and the residue was dissolved in a small amount of ethyl acetate and purified by fast column chromatography using 30%-50% ethyl acetate/hexane (600 mL) as eluent to afford the target product methyl 2-fluoro-6-nitrobenzoate (716 mg, 94% yield). The product characterization data were as follows: 1H NMR (400 MHz, CDCl3) δ 3.96 (s, 3H), 7.40-7.48 (m, 1H), 7.58 (td, J = 8.31,5.54 Hz, 1H), 7.94 (d, J = 8.31 Hz, 1H); mass spectrometry (MS) m/z 200.05 (MH+), calculated value ( C8H6FNO4) 199.03.