Reaktion #694526

Reaktionsgleichung

iodoxybenzoic acid

p-tolyl sulfide

→

title compound

Ausbeute 99.9%

Methyl phenyl sulfoxide

Ausbeute 99.9%

Lösungsmittel

CHCl3 H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe residual solids were removed by filtration
2. 2
   Waschenwashed with CHCl3 (40 mL)
3. 3
   WaschenThe combined filtrate was washed successively with saturated aq. NaHCO3 (30 mL), saturated aq. NaCl (30 mL)
4. 4
   Trocknendried over sodium sulfate
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto provide the crude product
7. 7
   SonstigePurification
8. 8
   Waschenby silica gel column chromatography (50% hexanes/EtOAc elution)

Vorschrift

To a stirred suspension of iodoxybenzoic acid (3.7 g, 13.2 mmol, 1.1 eq) in 100:1 CHCl3/H2O (25 mL) was added tetraethylammonium bromide (TEAB) (126 mg, 5 mol %), followed by the addition of p-tolyl sulfide (1.66 g, 12 mmol) in one portion. The mixture was stirred at room temperature for approximately 30 minutes until consumption of sulfide was observed (TLC, hexanes/EtOAc 1/1). The residual solids were removed by filtration and washed with CHCl3 (40 mL). The combined filtrate was washed successively with saturated aq. NaHCO3 (30 mL), saturated aq. NaCl (30 mL), dried over sodium sulfate, and concentrated to provide the crude product. Purification by silica gel column chromatography (50% hexanes/EtOAc elution) afforded the title compound (1.68 g, yield 91%). 1H NMR (300 MHz, CDCl3) δ 7.52 (d, J=8.4 Hz, 2H), 7.32 (d, J=8.4 Hz, 2H), 2.71 (s, 3H), 2.42 (s, 3H); ESI-MS m/z 154.7 (M+H)+.

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