Water → 4-Bromo-2-nitrobenzoic acid

HRID 1725896Notes

Reaction equation

HRID 1725896 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.N1C=CC=CC=1.[OH2:18].[Mn]([O-])(=O)(=O)=[O:20].[K+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:20])=[O:18])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 1235464-Bromo-2-nitrotolueneHCID 516875Potassium Permanganate

Product 1

HCID 37744674-Bromo-2-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-bromo-2-nitrotoluene (10 g, 46.2 mmol), pyridine (85 mL) and water (65 mL) was heated to reflux and treated portionwise with potassium permanganate (21.9 g, 138.9 mmol) over 8 hours. Ethanol (7.8 mL) was added and the mixture was filtered while hot through diatomaceous earth (Celite ®). The filtrate was concentrated and partitioned between water (200 mL), 10% NaOH (25 mL), and diethyl ether (250 mL). The aqueous phase was acidified to pH 1 with concentrated HCl and the resulting solid was collected by filtration and dried to provide the desired product. MS (ESI(−)) m/e 244, 246 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 14.06 (br s, 1H), 8.28 (d, 1H), 7.99 (dd, 1H), 7.81 (d, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationthe mixture was filtered while hot through diatomaceous earth (Celite ®)
  4. concentrationThe filtrate was concentrated
  5. custompartitioned between water (200 mL), 10% NaOH (25 mL), and diethyl ether (250 mL)
  6. filtrationthe resulting solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-7cb7aaf9adb0464da585a5c2d50a7ffb
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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