Nitric Acid → 5-Fluoro-2-nitrobenzoic acid

HRID 1157454Notes

Reaction equation

HRID 1157454 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[N+:11]([O-])([OH:13])=[O:12].O>S(=O)(=O)(O)O>[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:4]([CH:3]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 99683-Fluorobenzoic Acid

Product 1

HCID 27374205-Fluoro-2-nitrobenzoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 3-fluorobenzoic acid (7.9 g, 56 mmol) in conc. sulphuric acid (50 mL) cooled to 0° C. was added fuming nitric acid (4.7 g, 67 mmol) dropwise. After the addition the solution was warmed to room temperature and stirring continued for 1 h. The solution was poured into water (750 mL) and extracted with ethyl acetate (3×100 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to yield 5-fluoro-2-nitrobenzoic acid as a pale yellow solid (9.6 g, 52 mmol, 93%).

Workup

  1. additionAfter the addition the solution
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f36911a176f640868a2f5eda157895aa
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

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