Nitric Acid → Dimethyl 2-fluoro-5-nitrobenzene-1,4-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of dimethyl 2-fluoroterephthalate (42.0 g, 0.198 mol) in concentrated sulfuric acid (200 mL) at 0° C. was added 36 mL of a 1:1 mixture of nitric acid and sulfuric acid dropwise. The mixture was stirred at 0° C. for 15 min., the ice-bath was removed, and the reaction mixture was stirred for an additional 45 min. HPLC indicated that the starting material had been consumed. The reaction mixture was poured over ice and extracted with EtOAc. The organic layer was collected, washed with brine, and dried over anhydrous sodium sulfate. Concentration under reduced pressure followed by recrystallization from MeOH afforded 48.5 g (95%) of 174A as a white solid. HPLC retention time=2.69 min. (Condition B). 1H-NMR (500 MHz, CDCl3) δ 3.95 (s, 3H), 3.98 (s, 3H), 7.44 (d, 1H), and 8.59 (d, 1H).

Provenance & Evidence