Water → 2-(4-Bromo-2-methylphenyl)acetic acid

HRID 708856Notes

Reaction equation

HRID 708856 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:5]=1[CH3:11])[CH:2]=C.I([O-])(=O)(=O)=[O:13].[Na+].[OH2:18]>C(Cl)(Cl)(Cl)Cl.C(#N)C.O.[Ru](Cl)(Cl)Cl>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:1][C:2]([OH:13])=[O:18])=[C:5]([CH3:11])[CH:6]=1

Participants

7

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 534031561-Allyl-4-bromo-2-methylbenzene

Product 1

HCID 190260522-(4-Bromo-2-methylphenyl)acetic acidYield 88%

Reagents, catalysts & solvents 3

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 16A (12 g, 56.8 mmol) in CCl4 (200 mL), acetonitrile (200 mL) and water (300 mL) at rt was added ruthenium (III) chloride hydrate (1.474 g, 7.11 mmol) and sodium periodate (48.6 g, 227 mmol). The suspension was stirred vigorously for 5.0 h. The solvent was removed under vacuum. The residue was filtered though wet CELITE®, washed with EtOAc. The mixture was further extracted with EtOAc (3×400 mL). The volume of organic layers was reduced to ca 500 mL, washed with sat. sodium sulfite/with conc. HCl (pH ca 2-3). The organic layer was dried over sodium sulfate and concentrated. After evaporation of solvent, 16B (11.47 g, 50.1 mmol, 88% yield) was obtained as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.27 (s, 3H) 3.60 (s, 2H) 7.04 (d, J=7.91 Hz, 1H) 7.28 (dd, J=8.13, 1.98 Hz, 1H) 7.32 (s, 1H).

Workup

  1. customThe solvent was removed under vacuum
  2. filtrationThe residue was filtered though wet CELITE®
  3. washwashed with EtOAc
  4. extractionThe mixture was further extracted with EtOAc (3×400 mL)
  5. washwashed with sat. sodium sulfite/with conc. HCl (pH ca 2-3)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. customAfter evaporation of solvent

Sources & evidence

ORD record
ord-c7c123501fae4b4f829a461ac3c66e83
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

Loading…