Water → 4-Bromo-[1,1'-biphenyl]-2-carboxylic acid

HRID 1043414Notes

Reaction equation

HRID 1043414 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([CH3:14])[CH:3]=1.[Mn]([O-])(=O)(=O)=[O:16].[K+].[OH2:21]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=[O:21])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 99648454-Bromo-2-methylbiphenyl

Product 1

HCID 199224694-Bromo-[1,1'-biphenyl]-2-carboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-bromo-2-methylbiphenyl (5 g, 20.23 mmol) was suspended in pyridine (23 mL) and water (35 mL). Potassium permanganate (16 g, 101 mmol) was added portion wise over a period of 20 min. The mixture was refluxed overnight. The reaction mixture was cooled and MnO2 was filtered off. Conc. HCl was added to the filtrate until the product precipitated. The product was extracted with DCM, washed with water and brine, collected, dried (MgSO4), filtered and evaporated to give 4-bromobiphenyl-2-carboxylic acid (5 g, 18.04 mmol, 89% yield) as a white solid. LCMS: rt=1.39 min.; Phenomenex-Luna C-18 (5μ) (3.0×50 mm); Solvent A=10% acetonitrile—90% water—0.1% TFA, Solvent B=90% acetonitrile—10% water—0.1% TFA; gradient 0% to 100% solvent B over 2 min. and then hold for 1 min.; 4 mL/min; inj. vol.=5 uL; wavelength=220.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. filtrationMnO2 was filtered off
  4. additionConc. HCl was added to the filtrate until the product
  5. customprecipitated
  6. extractionThe product was extracted with DCM
  7. washwashed with water and brine
  8. customcollected
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-29868b549e6142709f9143c19db7f506
Source dataset
uspto-grants-2013_10
Patent number
US08563505B2

Reaction notes

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