Di-p-tolyl sulphide → Methyl phenyl sulfoxide

HRID 607344

Reaktionsgleichung

Reaktionsgleichung von HRID 607344
I(C1C=CC=CC=1C(O)=O)(=O)=[O:2].[C:13]1(C)[CH:18]=[CH:17][C:16]([S:19][C:20]2C=CC(C)=CC=2)=[CH:15][CH:14]=1>[Br-].C([N+](CC)(CC)CC)C.C(Cl)(Cl)Cl.O>[C:16]1([S:19]([CH3:20])=[O:2])[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1

Komponenten

5

Edukt 2

HCID 69294Di-p-tolyl sulphideHCID 1087942-Iodoxybenzoic acid

Produkt 1

HCID 14516Methyl phenyl sulfoxideAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6285Tetraethylammonium BromideKatalysatorHCID 22418719Chloroform waterLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  1. customThe residual solids were removed by filtration
  2. washwashed with CHCl3 (40 mL)
  3. washThe combined filtrate was washed successively with saturated aq. NaHCO3 (30 mL), saturated aq. NaCl (30 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto provide the crude product
  7. customPurification
  8. washby silica gel column chromatography (50% hexanes/EtOAc elution)

Quellen und Nachweise

ORD-Eintrag
ord-dae94bc90b4e40c9bfccf2a358742dc0
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915443B2

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