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

HRID 2180681

反応式

HRID 2180681 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 22492571Methyl 2-(3,5-dimethylphenyl)sulfanylbenzoate収率 86.6%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-3a3180a0f22e4428923fba8186046a1e
出典データセット
uspto-grants-2005_05
特許番号
US06888032B2

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