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

HRID 869802Notes

Reaction equation

HRID 869802 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 (Preparation 1b, 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-9424a19bd50d41c6ac536443af4442c2
Source dataset
uspto-grants-2015_03
Patent number
US08969350B2

Reaction notes

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