Potassium Carbonate → Methyl 2-(3,5-dimethylphenyl)sulfanylbenzoate

HRID 2253529

Reaktionsgleichung

Reaktionsgleichung von HRID 2253529
I[C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:10]([O:19][CH3:20])(=[O:18])[C:11]1[C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)[SH:13].C([O-])([O-])=O.[K+].[K+]>[Cu]I.COCCOC>[CH3:8][C:6]1[CH:7]=[C:2]([S:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[C:10]([O:19][CH3:20])=[O:18])[CH:3]=[C:4]([CH3:9])[CH:5]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 1409241-Iodo-3,5-dimethylbenzene

Produkt 1

HCID 22492571Methyl 2-(3,5-dimethylphenyl)sulfanylbenzoateAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

The general procedure in example 39 was followed. 5-Iodo-m-Xylene (144 μL, 1.0 mmol), Methyl thiosalicylate (138 μL, 1.0 mmol), CuI (10 mg, 0.05 mmol), K2CO3 (276 mg, 2.0 mmol), and DME (1.0 mL) were used to obtain the methyl 2-(3,5-dimethylphenyl)sulfanylbenzoate (236 mg, 86% yield) as colorless liquid. Column chromatographic solvent (hexane/ethyl acetate=20/1). Rf=0.5 (hexane/ethyl acetate=10/1). 1H NMR (CDCl3, 300 MHz) δ 7.95 (dd, 1 H, J=1.8 Hz, 8.1 Hz), 7.19-7.25 (m, 1 H), 7.17 (s, 2 H), 7.08 (dt, 1 H, J=1.2 Hz, 7.8 Hz), 7.03 (s, 1 H), 6.81 (dd, 1 H, J=0.9 Hz, 8.1 Hz), 3.94 (s, 3 H), 2.32 (s, 6 H). 13C NMR (CDCl3, 75 MHz) δ 170.0, 144.0, 139.6, 133.4, 132.5, 131.2, 127.4, 126.5, 124.2, 117.1, 52.5, 21.6. IR (neat, cm−1) 2950, 2916, 1712, 1711. MS (EI) m/z (relative intensity) 272 (100), 197 (70). HRMS (EI), Cald. for C16H16O2S 272.0866; Found 272.0858.

Quellen und Nachweise

ORD-Eintrag
ord-694bd84f4fe44e73aa426966a845dc77
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07323608B2

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