Nitric Acid → 5-Fluoro-2-nitrobenzoic acid

HRID 362909Notes

Reaction equation

HRID 362909 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10]>OS(O)(=O)=O>[F:5][C:6]1[CH:14]=[CH:13][C:12]([N+:1]([O-:4])=[O:2])=[C:8]([CH:7]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 99683-Fluorobenzoic Acid

Product 1

HCID 27374205-Fluoro-2-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Step 2): Conc. HNO3 (25 ml) was added dropwise to a solution of 3-fluorobenzoic acid (25 g, 178 mmol) in conc. H2SO4 (190 ml) under cooling in an ice-bath and stirring for 30 mins. After the addition was complete, the mixture was stirred at 0° C. and at room temperature for each 30 mins. The resulting solution was poured into an ice water and extracted with AcOEt. The extract was washed with brine, dried over MgSO4 and evaporated to give 5-fluoro-2-nitrobenzoic acid as yellow powder, 32.1 g (97.2%): mp 141°-142° C.

Workup

  1. temperatureunder cooling in an ice-bath
  2. additionAfter the addition
  3. stirringthe mixture was stirred at 0° C. and at room temperature for each 30 mins
  4. extractionextracted with AcOEt
  5. washThe extract was washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-20f8b86addfd486b9c91d791ff24d38c
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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