Nitric Acid → HCID 67403309, compound

HRID 906169Notes

Reaction equation

HRID 906169 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([F:13])[CH:4]=1)#[N:2].[N+:14]([O-])([OH:16])=[O:15].S(=O)(=O)(O)O>>[C:1]([C:3]1[C:12]([N+:14]([O-:16])=[O:15])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([F:13])[CH:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 15278726Methyl 4-cyano-2-fluorobenzoate

Product 1

HCID 67403309HCID 67403309, compoundYield 43%

Conditions

Temperature
45 °C

Procedure

To a flask containing methyl 4-cyano-2-fluorobenzoate (1.61 g, 9.0 mmol) was added fuming nitric acid (15 mL) followed by concentrated sulfuric acid (4 mL). The mixture was heated to 45° C. for 15 h before cooling to room temperature. The solution was then poured into ice water and the resulting mixture was extracted twice with ethyl acetate. The combined organic extracts were washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, filtered, and concentrated to provide methyl 4-cyano-2-fluoro-5-nitrobenzoate (859 mg, 3.83 mmol, 43% yield).

Workup

  1. temperaturebefore cooling to room temperature
  2. extractionthe resulting mixture was extracted twice with ethyl acetate
  3. washThe combined organic extracts were washed with saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-81290a7d63844428bbe23f676fd2a7be
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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