Sulfuric Acid → 2,3-Difluoro-5-nitrobenzoic acid

HRID 2171223Notes

Reaction equation

HRID 2171223 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[Na+].S(=O)(=O)(O)O.[F:11][C:12]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]>>[F:11][C:12]1[C:20]([F:21])=[CH:19][C:18]([N+:1]([O-:4])=[O:2])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24268Sodium NitrateHCID 3705902,3-Difluorobenzoic acid

Product 1

HCID 545937902,3-Difluoro-5-nitrobenzoic acidYield 79.3%

Procedure

Sodium nitrate (1.7 g) was added to a concentrated sulfuric acid (7 ml) solution containing 2,3-difluorobenzoic acid (1.58 g), followed by stirring at room temperature for 0.5 hours. The reaction solution was poured into ice water, followed by extraction with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 4:1). A light yellow solid of 2,3-difluoro-5-nitrobenzoic acid (1.61 g) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled away under reduced pressure
  4. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 4:1)

Sources & evidence

ORD record
ord-740305b99cd64764a2fa43807f540aea
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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