Potassium Nitrate → 2-Chloro-5-fluoro-4-methyl-3-nitro-benzoic acid

HRID 1697341Notes

Reaction equation

HRID 1697341 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:10]([N+:13]([O-:15])=[O:14])=[C:9]([CH3:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 136574382-Chloro-5-fluoro-4-methylbenzoic acid

Product 1

HCID 136574392-Chloro-5-fluoro-4-methyl-3-nitro-benzoic acidYield 102.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-chloro-5-fluoro-4-methylbenzoic acid (Example 252b, 51.57 g) dissolved in conc sulfuric acid (143 mL) was treated with potassium nitrate (32.4 g) portionwise over 10 min at 0° C. under nitrogen. The resulting mixture was allowed to warm to room temperature before stirring at 50° C. for 1 h. The reaction mixture was quenched with ice water and the precipitate was collected and dried in vacuo to afford the subtitle compound (65.5 g).

Workup

  1. customThe reaction mixture was quenched with ice water
  2. customthe precipitate was collected
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a5eeb019b44547ffabab1f782097f6cc
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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