Methanol → Methyl 4-fluoro-3-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-fluoro-3-nitro-benzoic acid (25 g, 0.135 mol) in dichloromethane (250 ml) at 23° C. was added dimethylformamide (0.5 ml) followed by dropwise addition of oxalyl chloride (15 ml, 0.172 mol). After stirring for 2 hours an aliquot was removed and confirmed to be product by 1H NMR. The entire sample was then concentrated under reduced pressure, diluted with dichloromethane (250 ml) and cooled to 0° C. The sample was then treated with a solution of triethylamine (37 ml, 0.266 mol) and methyl alcohol (43 ml, 0.939 mol) in dichloromethane (50 ml) added dropwise over 30 minutes. The reaction was allowed to warm to 23° C. After 2 hours the reaction was poured onto aqueous sodium bicarbonate and extracted with dichloromethane. The organic layer was dried with sodium sulfate and concentrated in vacuo to give 26.5 g of 4-fluoro-3-nitro-benzoic acid methyl ester as a solid.

Provenance & Evidence