Nitric Acid → 4-Fluoro-2-methyl-5-nitrobenzoic acid

HRID 1481867Notes

Reaction equation

HRID 1481867 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[F:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([CH3:20])[CH:12]=1>>[F:10][C:11]1[C:19]([N+:1]([O-:4])=[O:2])=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([CH3:20])[CH:12]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 38606394-Fluoro-2-methylbenzoic acid

Product 1

HCID 223131014-Fluoro-2-methyl-5-nitrobenzoic acid

Conditions

Temperature
0 °C

Procedure

A cooled mixture of fuming nitric acid (2.5 mL) and conc. sulfuric acid (25 mL) was slowly added to 4-fluoro-2-methyl-benzoic acid (9 g, 58.3 mmol) at 0° C. under N2 atmosphere over a period of 45 min. Reaction mixture was allowed to stir at 0° C. for 1 h. Starting material consumption was monitored by the TLC. Upon completion of the reaction the reaction mass was poured onto crushed ice and extracted in ethyl acetate (3×100 mL). Combined extract was washed with water, brine solution and dried over anhydrous Na2SO4. The solid obtained was washed with pet ether to afford the pure product 4-fluoro-2-methyl-5-nitro-benzoic acid.

Workup

  1. customReaction mixture
  2. customStarting material consumption
  3. customUpon completion of the reaction the reaction mass
  4. additionwas poured
  5. customonto crushed ice
  6. extractionextracted in ethyl acetate (3×100 mL)
  7. extractionCombined extract
  8. washwas washed with water, brine solution
  9. dry with materialdried over anhydrous Na2SO4
  10. customThe solid obtained
  11. washwas washed with pet ether

Sources & evidence

ORD record
ord-f72fbb3e3afc4457aa6a5ca86c3a89ac
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Reaction notes

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