Nitric Acid → HCID 67044866, compound

HRID 2367125Notes

Reaction equation

HRID 2367125 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[C:18]([F:19])=[CH:17][CH:16]=[C:15]([F:20])[C:11]=2[C:12]([OH:14])=[O:13])=[O:9])=[CH:4][CH:3]=1.[N+:21]([O-])([OH:23])=[O:22].S(=O)(=O)(O)O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[C:18]([F:19])=[CH:17][CH:16]=[C:15]([F:20])[C:11]=2[C:12]([OH:14])=[O:13])=[O:9])=[CH:6][C:7]=1[N+:21]([O-:23])=[O:22]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 44203047HCID 44203047, compound

Product 1

HCID 67044866HCID 67044866, compoundYield 74%

Conditions

Temperature
0 °C

Procedure

2-[(4-chlorophenyl)carbonyl]-3,6-difluorobenzoic acid (3.20 g, 11.00 mmol) was dissolved while heating in concentrated.sulfuric acid (15 ml) and it was cooled to 0° C. A solution of fuming nitric acid (0.5 ml, 11.00 mmol) in concentrated.sulfuric acid (3.0 mL) was added dropwise and the reaction mixture was stirred at 0° C. for 60 minutes. It was poured into crushed ice. The product was precipitated. It was collected by filtration then it was dissolved in ethyl acetate (100 mL); it was washed with water (2×40 mL), brine (40 mL) and dried over anhydrous sodium sulfate. Filtration and concentration resulted in a crude product, which was triturated with hexane. The crystalline product was collected by filtration to give 2-[(4-chloro-3-nitrophenyl)carbonyl]-3,6-difluorobenzoic acid (2.73 g, 74% yield). 1H NMR (400 MHz, CD3OD): 8.28 (s, 1H), 7.91 (d, J=8.8 Hz, 1H), 7.79 (d, J=8.4 Hz, 1H), 7.53-7.42 (m, 2H); MS (EI) for C14H7ClF2NO5: 341 (M−).

Workup

  1. temperaturewhile heating
  2. concentrationin concentrated
  3. additionIt was poured
  4. custominto crushed ice
  5. customThe product was precipitated
  6. filtrationIt was collected by filtration
  7. dissolutionit was dissolved in ethyl acetate (100 mL)
  8. washit was washed with water (2×40 mL), brine (40 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationFiltration and concentration
  11. customresulted in a crude product, which
  12. customwas triturated with hexane
  13. filtrationThe crystalline product was collected by filtration

Sources & evidence

ORD record
ord-f2443bd6afe54415a8c51b323925429a
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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