Nitric Acid → 2-Fluoro-4-methyl-5-nitrobenzoic acid

HRID 335317Notes

Reaction equation

HRID 335317 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[N+:17]([O-])([OH:19])=[O:18]>>[F:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([N+:17]([O-:19])=[O:18])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 27361452-Fluoro-4-methylbenzoic acid

Product 1

HCID 218947282-Fluoro-4-methyl-5-nitrobenzoic acid

Conditions

Temperature
0 °C

Procedure

2-Fluoro-4-methylbenzoic acid (1 g, 6.49 mmol) in H2SO4 (19 ml, 356 mmol) was cooled to 0° C. in an ice salt water bath and treated dropwise with mixture of H2SO4 (0.763 ml, 14.31 mmol) and nitric acid (0.65 ml, 14.54 mmol) over 10 min. The reaction mixture was stirred at 0° C. for 3 hrs and poured into ice/water (200 ml) and stirred for a further hour. The resulting suspension was collected by filtration, dried in vacuo and collected in EtOH, azeotroping to dryness to afford the title compound.

Workup

  1. stirringstirred for a further hour
  2. filtrationThe resulting suspension was collected by filtration
  3. customdried in vacuo
  4. customcollected in EtOH
  5. customazeotroping to dryness

Sources & evidence

ORD record
ord-d19ba5d61f3049b0b480d71e8720117f
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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