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

HRID 2070758Notes

Reaction equation

HRID 2070758 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-b7ee2b6af26f417687f92f5388f06ba7
Source dataset
uspto-grants-2012_10
Patent number
US08299246B2

Reaction notes

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