A kind of synthetic method of thioetherification and thiocarbonylation of halogenated alkanes
A technology of halogenated alkane sulfide and synthesis method, which is applied in the synthesis field of halogenated alkane thioetherification and thiocarbonylation, can solve the problems of complicated preparation of substrates, low yield, unpleasant odor and high toxicity of mercaptan, and the like, The method is simple, economical and practical
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Embodiment 1
[0041] To prepare 2-methylthio-4-p-methylphenylbutane, the reaction scheme is as follows:
[0042]
[0043] Add IPrCuCl (4.87mg, 0.01mol), NaO t Bu (76.8mg, 4equiv.) and dried stir bar. charging N 21-(3-Iodobutyl)-4-methylbenzene (0.2 mmol, 1 equiv.), methyl 3-(methylthio)propionate (0.6 mmol, 3 equiv.) and xylene (2 mL) were added under the same conditions. The resulting solution was heated to 140°C and the reaction was stirred at this temperature for 24 hours. Then, cool to room temperature. The solvent was removed under reduced pressure, and the crude product was purified by silica gel column chromatography, eluting with petroleum ether, and a colorless liquid (31 mg, 80%) was isolated.
[0044] The proton nuclear magnetic resonance spectrum analysis result is as follows:
[0045] 1 H NMR (600MHz, Chloroform-d) δ7.10(d, J=4.9Hz, 4H), 2.75–2.69(m, 2H), 2.66(p, J=6.8Hz, 1H), 2.33(d, J= 4.8Hz, 3H), 2.07(d, J=4.9Hz, 3H), 1.87(m, 1H), 1.77(m, 1H), 1.31(d, J=6.7Hz, 3H)....
Embodiment 2
[0053] To prepare 4-methylthiophenvalyl ether, the reaction scheme is as follows:
[0054]
[0055] Add IPrCuCl (4.87mg, 0.01mmol), NaO t Bu (76.8mg, 4equiv.) and dried stir bar. charging N 2 (4-Iodopentyloxy)benzene (0.2 mmol, 1 equiv.), methyl 3-(methylthio)propionate (0.6 mmol, 3 equiv.) and xylene (2 mL) were added under the same conditions. The resulting solution was heated to 140°C and the reaction was stirred at this temperature for 24 hours. Then, cool to room temperature. The solvent was removed under reduced pressure, and the crude product was purified by silica gel column chromatography, eluting with petroleum ether, and a colorless liquid (35 mg, 83%) was isolated.
[0056] The proton nuclear magnetic resonance spectrum analysis result is as follows:
[0057] 1 H NMR (600MHz, Chloroform-d) δ7.27(m,2H),7.01–6.80(m,3H),3.97(m,2H),2.73(h,J=6.8Hz,1H),2.08(s, 3H), 1.96–1.84 (m, 2H), 1.78–1.62 (m, 2H), 1.31 (d, J=6.7Hz, 3H).
[0058] The carbon NMR analysis re...
Embodiment 3
[0065] To prepare 2-methylthio-4-ethoxyphenylbutane, the reaction scheme is as follows:
[0066]
[0067] Add IPrCuCl (4.87mg, 0.01mmol), NaO t Bu (76.8mg, 4equiv.) and dried stir bar. charging N 2 Add 1-ethoxy-4-(3-iodobutyl)benzene (0.2mmol, 1equiv.), methyl 3-(methylthio)propanoate (0.6mmol, 3equiv.) and xylene (2mL) . Methyl 3-(methylthio)propionate (0.6 mmol, 3 equiv.) and xylene (2 mL). The resulting solution was heated to 140°C and the reaction was stirred at this temperature for 24 hours. Then, cool to room temperature. The solvent was removed under reduced pressure, and the crude product was purified by silica gel column chromatography, eluting with petroleum ether, and a colorless liquid (33 mg, 74%) was isolated.
[0068] The proton nuclear magnetic resonance spectrum analysis result is as follows:
[0069] 1 H NMR (600MHz, Chloroform-d) δ7.15–7.05(m,2H),6.85–6.76(m,2H),4.01(q,J=7.0Hz,2H),2.77–2.55(m,3H), 2.06(s, 3H), 1.85(m, 1H), 1.74(m, 1H), 1.39(t, J=...
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