Nitric Acid → 2-Chloro-4-fluoro-5-nitrobenzoic Acid

HRID 1940482Notes

Reaction equation

HRID 1940482 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[Cl:10][C:11]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]>C(OCC)(=O)C>[Cl:10][C:11]1[CH:19]=[C:18]([F:20])[C:17]([N+:1]([O-:4])=[O:2])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 752592-Chloro-4-fluorobenzoic acid

Product 1

HCID 72108282-Chloro-4-fluoro-5-nitrobenzoic AcidYield 99.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A blend of 70% nitric acid (64.5 gm) and concentrated sulfuric acid (65 mL) was added dropwise over an hour period to a suspension of 2-chloro-4-fluoro-benzoic acid (125.0 gm, 716 mL). The white suspension was stirred mechanically for 30 minutes at ambient temperature. The thick white suspension was carefully poured into ice-water (100 mL). Ethyl acetate (800 mL) was added. The organic layer was separated, dried (MgSO4) and evaporated to dryness under vacuum to give the title compound of Step A as a white solid (156.0 gm, 99%); m.p. 134°-136° C.; IR (cm-1), C=O (1719.8). This intermediate was used without further purification.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-c8f258b711684b759bb2e7b943597c76
Source dataset
uspto-grants-1997_12
Patent number
US05700761

Reaction notes

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