Nitric Acid → 2-Bromo-5-fluoro-3-nitrobenzoic acid

HRID 521409Notes

Reaction equation

HRID 521409 reaction equation
OS(O)(=O)=O.[N+:6]([O-:9])(O)=[O:7].[Br:10][C:11]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]>>[Br:10][C:11]1[C:19]([N+:6]([O-:9])=[O:7])=[CH:18][C:17]([F:20])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 27781812-Bromo-5-fluorobenzoic acid

Product 1

HCID 185485832-Bromo-5-fluoro-3-nitrobenzoic acidYield 49%

Procedure

To a 3 liter round bottom flask was charged with 500 ml H2SO4. Fuming nitric acid was added (40 mL) and the mixture gently stirred. 2-Bromo-5-fluorobenzoic acid (60 g, 219 mmol) was added in 5 g portions over 90 minutes at 5-10° C. The mixture was stirred for 60 minutes at which time the reaction was completed. The mixture was poured into 1 liter of an ice/water mixture and extracted with EtOAc (3×600 mL). The combined organic extracts are dried (MgSO4) and concentrated under reduced pressure to give a yellow solid. The solid was suspended in hexanes and stirred for 30 minutes. The solid was collected on filter to provide 2-bromo-5-fluoro-3-nitrobenzoic acid as yellow solid (35 g, 49%).

Workup

  1. stirringThe mixture was stirred for 60 minutes at which time the reaction
  2. extractionextracted with EtOAc (3×600 mL)
  3. dry with materialThe combined organic extracts are dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give a yellow solid
  6. stirringstirred for 30 minutes
  7. customThe solid was collected
  8. filtrationon filter

Sources & evidence

ORD record
ord-4b4f63e0307a4ecf82ed96ca7a6cc5f2
Source dataset
uspto-grants-2016_05
Patent number
US09328111B2

Reaction notes

Loading…