Nitric Acid → HCID 66859069, compound

HRID 1803150Notes

Reaction equation

HRID 1803150 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5](=[O:18])([O:15][CH2:16][CH3:17])[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[F:14]>S(=O)(=O)(O)O>[C:5](=[O:18])([O:15][CH2:16][CH3:17])[O:6][C:7]1[CH:12]=[C:11]([N+:1]([O-:4])=[O:2])[CH:10]=[C:9]([F:13])[C:8]=1[F:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 66858654HCID 66858654, compound

Product 1

HCID 66859069HCID 66859069, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

Step M (2): A mixture of concentrated sulfuric acid and nitric acid (1:1 ratio, 60 mL total volume) was slowly and carefully added to a solution of 2,3-difluorophenyl ethyl carbonate (20 g, 98.9 mmol) in concentrated sulfuric acid (15 mL). The internal temperature was maintained at rt throughout the addition. After complete addition, the resulting mixture was stirred for 2 h. The mixture was poured onto ice and extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (hexane) to afford 2,3-difluoro-5-nitrophenyl ethyl carbonate (1.5 g, 6% yield).

Workup

  1. additionAfter complete addition
  2. additionThe mixture was poured onto ice
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified

Sources & evidence

ORD record
ord-fcede2f1928047a58226bc08fade358b
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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