Water → 2-Bromo-4-fluoro-5-methoxybenzoic acid

HRID 335697Notes

Reaction equation

HRID 335697 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[Br:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([O:15][CH3:16])=[CH:10][C:9]=1[CH3:17].[OH2:18]>N1C=CC=CC=1>[Br:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([O:15][CH3:16])=[CH:10][C:9]=1[C:17]([OH:2])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 227282131-Bromo-5-fluoro-4-methoxy-2-methylbenzene

Product 1

HCID 534357102-Bromo-4-fluoro-5-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

Potassium permanganate (53 g, 3.4 mol) was added to a solution of 1-bromo-5-fluoro-4-methoxy-2-methylbenzene (37 g, 1.7 mol) in 75 ml of pyridine and 150 ml of water at 60° C. The solution was stirred at 60° C. degrees for 24 hours. The solution was filtered and the solids were washed with a solution of water/methanol (50:50). The filtrate was concentrated to approximately 100 ml, then acidified (pH 1) with concentrated HCl. The solid was collected by filtration and dried under vacuum to afford 2-bromo-4-fluoro-5-methoxybenzoic acid as an off white solid. MS m/z=248.9 [M+H].

Workup

  1. filtrationThe solution was filtered
  2. washthe solids were washed with a solution of water/methanol (50:50)
  3. concentrationThe filtrate was concentrated to approximately 100 ml
  4. filtrationThe solid was collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-6ff4b2eaefe94cb698ea5e7ac716e246
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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