Potassium Nitrate → 4-Fluoro-5-methyl-2-nitrobenzoic acid

HRID 532229Notes

Reaction equation

HRID 532229 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].[N+:12]([O-])([O-:14])=[O:13].[K+]>OS(O)(=O)=O>[F:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 2428284-Fluoro-3-methylbenzoic acid

Product 1

HCID 581158484-Fluoro-5-methyl-2-nitrobenzoic acidYield 104.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 4-fluoro-3-methylbenzoic acid (3.7 g, 24 mmol) in conc. H2SO4 (50 mL) at 0° C. was added KNO3 (3.6 g, 36 mmol) in one portion and the mixture was stirred at rt for 2 h. The reaction mixture was poured into ice water (200 mL) and extracted with DCM (100 mL×2). The organic layer was washed with brine, dried and concentrated to give the crude 4-fluoro-5-methyl-2-nitrobenzoic acid (5 g) as white solid. It was used in the next step without further purification.

Workup

  1. extractionextracted with DCM (100 mL×2)
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6b2da92a226841d982d1398b256a8e16
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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