Water → 4-Bromo-2-nitrobenzoic acid

HRID 430434Notes

Reaction equation

HRID 430434 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.[Mn]([O-])(=O)(=O)=[O:13].[K+].[OH2:18]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:13])=[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 acid

Conditions

Temperature
97 °C

Procedure

A suspension of 4-bromo-2-nitrotoluene (50 g) in water was heated to 97° C. Potassium permanganate (240 g) was then added over a period of 4.5 hours. The resulting suspension was heated at reflux overnight. The mixture was filtered whilst hot (through ‘HYFLO’ silica). The filter cake was washed through with boiling water. The cooled filtrates were washed with diethyl ether then acidified to pH 1 with concentrated hydrochloric acid. The resulting suspension was cooled in ice water and then filtered. The solid was dried to yield 4-bromo-2-nitrobenzoic acid (10.83 g) as a cream solid, m.p. 164-167° C.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux overnight
  3. filtrationThe mixture was filtered whilst hot (through ‘HYFLO’ silica)
  4. washThe filter cake was washed through with boiling water
  5. washThe cooled filtrates were washed with diethyl ether
  6. temperatureThe resulting suspension was cooled in ice water
  7. filtrationfiltered
  8. customThe solid was dried

Sources & evidence

ORD record
ord-14551e66009743d5a4a61fba09359889
Source dataset
uspto-grants-2001_11
Patent number
US06323155B1

Reaction notes

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