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

HRID 2253529

반응식

HRID 2253529 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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.

출처 및 근거

ORD 기록
ord-694bd84f4fe44e73aa426966a845dc77
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07323608B2

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