Di-p-tolyl sulphide → Methyl phenyl sulfoxide

HRID 607344

反応式

HRID 607344 の反応式
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

参加物

5

反応物 2

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

生成物 1

HCID 14516Methyl phenyl sulfoxide収率 99.9%

試薬・触媒・溶媒 2

HCID 6285Tetraethylammonium Bromide触媒HCID 22418719Chloroform water溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-dae94bc90b4e40c9bfccf2a358742dc0
出典データセット
uspto-grants-2011_03
特許番号
US07915443B2

関連ノート

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