Nitric Acid → 5-Fluoro-2-hydroxy-3-nitrobenzoic acid

HRID 415167Notes

Reaction equation

HRID 415167 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 676585-Fluorosalicylic acid

Product 1

HCID 152546965-Fluoro-2-hydroxy-3-nitrobenzoic acidYield 95.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a mixture of 5-fluoro-2-hydroxybenzoic acid (3.08 g, 19.76 mmol) in concentrated H2SO4 (30 mL) below 0° C. was added dropwise a mixture of concentrated HNO3 (2.11 g, 21.74 mmol) and concentrated H2SO4 (6 mL) with stirring below 5° C. After the addition, the mixture was stirred at this temperature for 2 hr. The reaction mixture was poured onto crash ice and the precipitate was collected, then the precipitate was dissolved in ethyl acetate (100 mL), washed with water (50 mL×2), brine (30 mL), dried over anhydrous sodium sulfate and concentrated to give 5-fluoro-2-hydroxy-3-nitrobenzoic acid (3.8 g) as a brown solid. LC-MS (ESI) m/z 202 [M+1]+.

Workup

  1. additionwas added dropwise
  2. additionAfter the addition
  3. stirringthe mixture was stirred at this temperature for 2 hr
  4. additionThe reaction mixture was poured onto crash ice
  5. customthe precipitate was collected
  6. dissolutionthe precipitate was dissolved in ethyl acetate (100 mL)
  7. washwashed with water (50 mL×2), brine (30 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ef830c2e675a436986d913f112be4bdb
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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