Nitric Acid → Methyl 4-fluoro-3-methyl-5-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

Concentrated H2SO4 (17.5 mL) was slowly added to methyl 4-fluoro-3-methylbenzoate (12.8 g, 76 mmol) and the mixture was cooled to 0° C. A solution of fuming HNO3 (69.5%, 11.6 mL) in concentrated H2SO4 (17.5 mL) was then added drop-wise over 10 min. The mixture was stirred for 80 min while slowly warming up to room temperature (reaction completion monitored by TLC). The mixture was slowly poured into ice, the aqueous layer was extracted with CH2Cl2 (3×200 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was purified by column chromatography to afford methyl 4-fluoro-3-methyl-5-nitrobenzoate (I-35a) as a white solid. MS calculated for C9H9FNO4 (M+H+) 214.04. found 214.0.

Provenance & Evidence