Nitric Acid → HCID 53416146, compound

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.

1. customThe reaction mixture was removed from the ice bath
2. additionThe reaction mixture was poured onto ice
3. additionwas diluted to ˜350 mL with H2O
4. extractionThe aqueous was extracted with EtOAc (3×)
5. washThe combined organic phase was washed with sat. NaHCO3 and brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated
8. dissolutionThe crude product was dissolved in EtOAc (10 mL)
9. additionwas diluted with hexanes (40 mL)
10. filtrationThe solution was filtered though a 1″ pad of SiO2
11. washthe pad was rinsed with 20% EtOAc/hexanes
12. concentrationThe filtrate was concentrated
13. dissolutionThe resultant oil was dissolved in chloroform
14. washeluted with a gradient from 0 to 15% EtOAc/hexanes

ORD record

ord-499967d668e644858976be145d63830e

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174974B2