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

Beteiligte Stoffe

Reaktionsschritte

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).

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