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Method for synthesizing (2-iodine-2-aryl) ethyl aryl ether derivatives

A technology of ethyl aryl ether and synthesis method, which is applied in thioether preparation, organic chemistry and other directions, can solve problems such as difficulty in obtaining β-iodothioether compounds, and achieves a wide range of substrate expansion and group tolerance. The effect of good sex and considerable profit

Inactive Publication Date: 2019-07-16
JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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  • Abstract
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AI Technical Summary

Problems solved by technology

Using this free radical oxidation strategy, it is difficult to obtain β-iodothioether compounds

Method used

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  • Method for synthesizing (2-iodine-2-aryl) ethyl aryl ether derivatives
  • Method for synthesizing (2-iodine-2-aryl) ethyl aryl ether derivatives
  • Method for synthesizing (2-iodine-2-aryl) ethyl aryl ether derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the synthesis of (2-iodo-2-phenyl) ethyl p-cresyl ether

[0024]

[0025] Add styrene (0.4mmol, 41.6mg), N-iodosuccinimide (0.1mmol, 22.5mg), p-methyldiphenyl disulfide (0.2mmol, 49.2mg), iodine Cuprous chloride (0.4eq, 7.6mg), o-phenanthroline (0.4eq, 7.9mg), 1,2-dichloroethane (2mL), magnetically stirred at 80°C for 1 hour; Extract with ethyl ester, combine the organic phases, evaporate most of the solvent under reduced pressure to obtain the crude product, use petroleum ether: ethyl acetate (20:1) as eluent to carry out column chromatography separation and purification to the crude product, and obtain the target product It is a light yellow solid with a yield of 68%.

[0026] Its NMR data are as follows:

[0027] 1 H NMR (300MHz, CDCl 3 )δ=7.34~7.25(m, 4H), 7.21~7.18(d, J=8.1Hz, 1H), 7.12~7.06(m, 4H), 4.23~4.18(dd, J=4.8Hz, J=10.2Hz ,1H), 3.51~3.45(dd, J=5.1Hz, J=13.5Hz, 1H), 3.36~3.28(dd, J=10.2Hz, J=13.2Hz, 1H), 2.34(s,3H).

Embodiment 2

[0028] Embodiment 2: the synthesis of (2-iodo-2-(4'-nitrophenyl)) ethyl p-cresyl ether

[0029]

[0030] Add 4-nitrostyrene (0.4mmol, 59.6mg), N-iodosuccinimide (0.1mmol, 22.5mg), p-methyldiphenyl disulfide (0.2mmol, 49.2 mg), cuprous iodide (0.4eq, 7.6mg), o-phenanthroline (0.4eq, 7.9mg), 1,2-dichloroethane (2mL), magnetically stirred at 80°C for 1 hour; Finally, extract with ethyl acetate, combine the organic phases, evaporate most of the solvent under reduced pressure to obtain the crude product, use sherwood oil: ethyl acetate (10:1) as the eluent to carry out column chromatography separation and purification for the crude product, The target product was obtained as a brown-yellow solid with a yield of 70%.

[0031] Its NMR data are as follows:

[0032] 1 H NMR (300MHz, CDCl 3 )δ=7.42(d, J=8.1Hz, 2H), 7.19(d, J=8.1Hz, 2H), 7.11~7.05(m, 4H), 4.18~4.13(dd, J=4.8Hz, J=10.5 Hz, 1H), 3.50~3.44(dd, J=4.5Hz, J=13.5Hz, 1H), 3.30~3.22(dd, J=10.2Hz, J=13.5Hz, 1H), 2.36(s, 3H...

Embodiment 3

[0033] Embodiment 3: the synthesis of (2-iodo-2-(4'-fluorophenyl)) ethyl p-cresyl ether

[0034]

[0035] Add 4-fluorostyrene (0.4mmol, 48.8mg), N-iodosuccinimide (0.1mmol, 22.5mg), p-methyldiphenyl disulfide (0.2mmol, 49.2mg) into a 25mL reaction tube ), cuprous iodide (0.4eq, 7.6mg), o-phenanthroline (0.4eq, 7.9mg), 1,2-dichloroethane (2mL), magnetically stirred at 80°C for 1 hour; , extract with ethyl acetate, combine the organic phases, evaporate most of the solvent under reduced pressure to obtain the crude product, use petroleum ether: ethyl acetate (10:1) as eluent to carry out column chromatography separation and purification to the crude product, obtain The target product is a light yellow solid with a yield of 70%.

[0036] Its NMR data are as follows:

[0037] 1 H NMR (300MHz, CDCl 3 )δ=7.27~7.18(m,3H),7.16~7.07(m,4H),7.05~6.94(m,1H),4.20~4.15(dd,J=4.5Hz,J=10.2Hz,1H),3.49 ~3.43 (dd, J=4.8Hz, J=13.5Hz, 1H), 3.29~3.21 (dd, J=10.2Hz, J=13.5Hz, 1H), 2.33 (s, 3H)...

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Abstract

The invention discloses a method for synthesizing (2-iodine-2-aryl) ethyl aryl ether derivatives, belonging to the technical field of organic synthesis intermediates. The method comprises the following steps: 1) adding styrene derivative, diaryl disulfide, N-iodosuccinimide and 1,2-dichloroethane, tightening the bottle stopper of a reaction tube, and magnetically stirring for 1 hour at 80 DEG C; 2) after that reaction, extracting ethyl acetate, combining the organic phases, distilling under reduced pressure to remove most of the solvent to obtain crude product, and carrying out column chromatography separation and purification on the crude product with petroleum ether and ethyl acetate in a volume ratio of 5:1-30:1 as eluent to obtain the target product. The method has wide application inmedicine, pesticide, chemical industry, organic synthesis and many other fields. In addition, the invention has the advantages of simple operation, mild reaction conditions, low cost, high yield and good application prospect.

Description

technical field [0001] The invention belongs to the field of organic synthesis intermediates, and relates to the use of cuprous iodide to catalyze the three-component reaction of styrene derivatives, diaryl disulfides, and N-iodosuccinimide to obtain (2-iodo- The synthetic method of 2-aryl) ethyl aryl ethers. Background technique [0002] Organic thioether compounds are important intermediates in organic synthesis and can be widely used in chemical industry, materials, pesticides and other fields. In recent years, the synthetic methods of these compounds have attracted much attention. We envisioned the introduction of an iodine atom into the alkyl chain of the thioether compound molecule while constructing it. Because this alkyl iodide undergoes further nucleophilic substitution reactions with a variety of nucleophilic reagents, it can also participate in transition metal-catalyzed coupling reactions, so that various functionalized thioether compounds can be obtained. Rec...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C323/07
CPCC07C319/14C07C323/07
Inventor 严国兵张洁雨何平于健张玲
Owner JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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