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A kind of preparation method of efficient 1-aryl-4-butene compound

A compound and aryl technology, applied in the field of fine chemicals and related chemistry, to achieve the effects of high yield, easy operation and mild reaction conditions

Active Publication Date: 2021-05-07
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This synthetic method can only obtain aromatic hydrocarbon allylation products, but involves the direct coupling reaction of halomethyl aromatic compounds and allyl boron compounds catalyzed by transition metal palladium to prepare 1-aryl-4-butene compounds The method has not been reported yet

Method used

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  • A kind of preparation method of efficient 1-aryl-4-butene compound
  • A kind of preparation method of efficient 1-aryl-4-butene compound
  • A kind of preparation method of efficient 1-aryl-4-butene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: the synthesis of p-methyl-3-butenylbenzene

[0048] In a 25mL reactor, add 4-methylbenzyl chloride (0.028g, 0.2mmol), allylboronic acid pinacol ester (0.067g, 0.4mmol), palladium acetate (2.2mg, 0.01mmol), cesium fluoride (0.091g, 0.6mmol), 4,5-bisdiphenylphosphine-9,9-dimethylxanthene (8.7mg, 0.015mmol), stirred at 80°C for 12h under nitrogen. Column chromatography separation (silica gel, 200-300 mesh; developer, petroleum ether) gave 0.023 g of p-methyl-3-butenylbenzene with a yield of 83%.

[0049] p-Methyl-3-butenylbenzene

[0050] colorless oily liquid; 1 H NMR (400MHz, CDCl 3):δ7.09(s,4H),5.92–5.80(m,1H),5.08–4.94(m,2H),2.67(t,J=8.0Hz,2H),2.36(q,J=8.0Hz, 2H), 2.32(s, 3H); 13 C NMR (100MHz, CDCl 3 ): δ139.8, 138.2, 135.2, 128.9, 128.3, 114.8, 35.6, 34.9, 21.0.

Embodiment 2

[0051] Embodiment 2: the synthesis of p-ethyl-3-butenylbenzene

[0052] The operation was the same as in Example 1, and 0.024 g of p-ethyl-3-butenylbenzene was obtained from the reaction of 4-ethylbenzyl chloride and allylboronic acid pinacol ester, with a yield of 79%.

[0053] p-Ethyl-3-butenylbenzene

[0054] colorless oily liquid; 1 H NMR (400MHz, CDCl 3 ):δ7.11(s,4H),5.92–5.90(m,1H),5.09–4.95(m,2H),2.68(t,J=8.0Hz,2H),2.62(q,J=8.0Hz, 2H), 2.36(q, J=8.0Hz, 2H), 1.22(t, J=8.0Hz, 3H); 13 C NMR (100MHz, CDCl 3 ): δ141.7, 139.1, 138.3, 128.4, 127.8, 114.8, 35.6, 34.9, 28.5, 15.7.

Embodiment 3

[0055] Embodiment 3: the synthesis of p-tert-butyl-3-butenylbenzene

[0056] The operation is the same as in Example 1, and 0.030 g of p-tert-butyl-3-butenylbenzene is obtained by reacting 4-tert-butylbenzyl chloride with allylboronic acid pinacol ester, and the yield is 82%.

[0057] p-tert-Butyl-3-butenylbenzene

[0058] colorless oily liquid; 1 H NMR (400MHz, CDCl 3 ):δ7.35(d, J=8.0Hz, 2H), 7.18(d, J=8.0Hz, 2H), 5.98–5.96(m, 1H), 5.14–4.99(m, 2H), 2.76–2.69( t,J=8.0Hz,2H), 2.44–2.39(m,2H),1.36(s,9H); 13 C NMR (100MHz, CDCl 3 ): δ148.6, 138.8, 138.3, 128.1, 125.2, 114.8, 35.5, 34.8, 34.4, 31.4.

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Abstract

The invention belongs to the field of fine chemicals and related chemical technologies, and provides a highly efficient preparation method of 1-aryl-4-butene compounds. Using halogen-containing methyl aromatic hydrocarbons and their derivatives as raw materials, in the presence of palladium catalysts and ligands, cesium fluoride as a base, under the condition of anhydrous organic solvents, and allylboronic acid pinacol ester at 80 ° C ~ 1-aryl-4-butene compound can be obtained by reacting at 100°C for 12 hours. The invention has the beneficial effects of high selectivity, mild reaction conditions, easy and convenient operation, the possibility of realizing industrialization, and obtaining 1-aryl-4-butene compounds in a relatively high yield; the 1-aryl-4-butene compound synthesized by the method is Aryl-4-butene compounds can be further functionalized to obtain various compounds, which are applied in the development and research of natural products, functional materials and fine chemicals.

Description

technical field [0001] The invention belongs to the field of fine chemicals and related chemical technologies, and provides a highly efficient preparation method of 1-aryl-4-butene compounds. Background technique [0002] 1-aryl-4-butene compounds are an extremely important structural unit in organic chemistry, and they are very important in the fields of medicine, pesticides, dyes, spices and functional materials [Macromolecules2011,44,4167-4179] application value. Among them, 1-phenyl-4-butene is used as the core raw material for the synthesis of antihypertensive drug fosinopril sodium. [0003] The reported synthesis methods of 1-aryl-4-butene compounds include Grignard reaction method [Org.Lett.2014,16,1610-1613], electrocatalytic alkylation method [Org.Lett.2017,19, 2022-2025], alkyne reduction method [Chem.Lett.2011,40,405-407], etc. [0004] The Grignard reaction method is the most common synthetic method, that is, the raw material containing allyl is reacted with ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C1/32C07C15/44C07C15/50C07C253/30C07C255/50C07C67/343C07C69/76C07C15/58
CPCC07C1/321C07C67/343C07C253/30C07C2531/22C07C15/44C07C15/50C07C15/58C07C255/50C07C69/76
Inventor 张胜尹俊超包明冯秀娟
Owner DALIAN UNIV OF TECH
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