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

HRID 22634

Reaction equation

HRID 22634 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

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

Product 1

HCID 72108282-Chloro-4-fluoro-5-nitrobenzoic Acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 2-chloro-4-fluorobenzoic acid (24.4 g, 0.142 mol) in 150 ml of concentrated sulfuric acid at 0° C. was treated dropwise with 90% nitric acid (13.2 ml, 20 mol %, 0.284 mol) over a 10 min. period at 10° C., stirred for 2.5 hours at 0 to 10° C., poured onto one liter of ice. The white solid was filtered. The filtercake was air-dried and recrystallized from ethyl acetate/heptane to afford the title compound as off-white needles. Yield: 18.0 g (58.1%); identified by NMR spectral analysis.

Workup

  1. filtrationThe white solid was filtered
  2. customThe filtercake was air-dried
  3. customrecrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-82b51a0afe8b45b9b3dbcd705924a1bb
Source dataset
uspto-grants-2005_02
Patent number
US06849618B2

Linked notes

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