Nitric Acid → HCID 53416146, compound

Participants

Reaction Steps

To a solution of 2,3-difluorobenzaldehyde (2.9 g, 20.41 mmol) in conc. sulfuric acid (18 mL, 324 mmol) at 0° C., was added nitric acid (70%) (3.6 mL, 56.4 mmol) dropwise. The reaction mixture was removed from the ice bath and was stirred at rt for 3 h. The reaction mixture was poured onto ice, then was diluted to ˜350 mL with H2O. The aqueous was extracted with EtOAc (3×). The combined organic phase was washed with sat. NaHCO3 and brine, dried (Na2SO4) and concentrated. The crude product was dissolved in EtOAc (10 mL), then was diluted with hexanes (40 mL). The solution was filtered though a 1″ pad of SiO2, then the pad was rinsed with 20% EtOAc/hexanes. The filtrate was concentrated. The resultant oil was dissolved in chloroform and hexanes, loaded onto a 150 g column and eluted with a gradient from 0 to 15% EtOAc/hexanes to give 11A (1.345 g, 7.19 mmol, 35.2% yield) as a colorless oil.

Provenance & Evidence