関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | Benzoic acid, 2-mercapto-, methyl ester | HCID 21009 | — |
| 反応物 | 1-Iodo-3,5-dimethylbenzene | HCID 140924 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 生成物 | Methyl 2-(3,5-dimethylphenyl)sulfanylbenzoate | HCID 22492571 | 86.6% |
反応手順
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.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US06888032B2 |
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| 出典データセット | uspto-grants-2005_05 |
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| ORD ID | ord-3a3180a0f22e4428923fba8186046a1e |
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| 出典メモ | uspto-grants-2005_05 |
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