Unlock instant, AI-driven research and patent intelligence for your innovation.
A kind of preparation method of efficient 1-aryl-4-butene compound
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
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
View PDF2 Cites 0 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
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 metalpalladium to prepare 1-aryl-4-butene compounds The method has not been reported yet
Method used
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
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, petroleumether) gave 0.023 g of p-methyl-3-butenylbenzene with a yield of 83%.
[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%.
[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%.
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
PUM
Login to View More
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
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to View More 
Login to View More 
