Water → 4-Bromo-2-nitrobenzoic acid

HRID 2265211Notes

Reaction equation

HRID 2265211 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[O-:12][Mn](=O)(=O)=O.[K+].[OH2:18]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:12])=[O:18])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 1235464-Bromo-2-nitrotolueneHCID 516875Potassium Permanganate

Product 1

HCID 37744674-Bromo-2-nitrobenzoic acidYield 22%

Procedure

A mixture of 4-bromo-2-nitrotoluene (5.0 g, 23 mmol), KMnO4 (10.9 g, 69 mmol), and water (250 mL) was heated at reflux overnight. The mixture was filtered through a pad of diatomaceous earth, washing with water. The basic filtrate was acidified to pH˜1 with conc. HCl and extracted with EtOAc (3×300 mL). The combined organic layers were dried (MgSO4) and concentrated to provide the desired benzoic acid (1.22 g, 22%). MS (ESI−): mass calcd. for C7H4BrNO4, 244.9; m/z found, 244 [M−H]−. 1H NMR (400 MHz, CD3OD): 8.07 (d, J=1.9, 1H), 7.85 (dd, J=8.2, 1.9, 1H), 7.65 (d, J=8.2, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationThe mixture was filtered through a pad of diatomaceous earth
  4. washwashing with water
  5. extractionextracted with EtOAc (3×300 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fcf0284fd3754bd99e7adc767ae22065
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

Loading…