Unlock instant, AI-driven research and patent intelligence for your innovation.
Synthesis method of novel difluoromethylene phosphate salt, and application of novel difluoromethylene phosphate salt
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 technology of difluoromethylene phosphonium and alkyl, which is applied in the field of organic synthesis and can solve problems such as lack of wittig reagents
Active Publication Date: 2014-08-06
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
View PDF1 Cites 7 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
However, there is still a lack of satisfactory methods for the mild and efficient preparation of Wittig reagents
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
preparation example Construction
[0149] Preparation of Difluoromethylenephosphonium Inner Salt Compound
[0150] The preparation method of said compound comprises:
[0151] In an inertsolvent, XCF 2 CO 2 - m + with (R 1 R 2 R 3 ) P reacts to form a compound of formula A;
[0152] Wherein, X is a leaving group, including (but not limited to) easy leaving groups such as Cl, Br, I, -OTf, -OTs, -OMs, or combinations thereof;
[0154] In the formula, R 1 , R 2 , R 3 is defined as above.
[0155] Or the compound of formula A can be prepared by the following method:
[0156] In an inertsolvent, the XCF 2 CO 2 Si(R 4 R 5 R 6 ) and (R 1 R 2 R 3 )P reacts with fluorine anions to obtain (R 1 R 2 R 3 ) P + CF 2 CO 2 - ;
[0157] XCF 2 CO 2 Si(R 4 R 5 R 6 )+(R 1 R 2 R 3 )P+fluoride anion→(R 1 R 2 R ...
Embodiment 1
[0233] In a 25mL single-necked bottle, the Ph 3 P (2.62g, 10mmol) with ClCF 2 COOLi (1.36g, 10mmol) was dissolved in a mixed solvent of ethanol and dimethyl sulfoxide, and sealed at 0°C for 20h. Then stop the reaction, filter to obtain a white solid, wash with dimethyl sulfoxide two to three times, and then wash with ether three times, then dissolve the obtained solid in isobutanol, and evaporate the upper clear solution to dryness under reduced pressure to obtain the product ( 3.20 g), isolated yield: 90%.
[0234] Ph 3 P + CF 2 CO 2 - : 1 H NMR (300MHz, MeOD) δ7.89-7.61 (m, 15H), 19 FNMR (282MHz, CDCl 3 ) δ - 91.47 (d, 2F).
Embodiment 2
[0236] In a 25mL single-necked bottle, the Ph 3 P (2.62g, 10mmol) with BrCF 2 COOK (2.12g, 10mmol) was dissolved in N,N-dimethylformamide, and the reaction was sealed at 25°C for 10h. Then stop the reaction, filter to obtain a white solid, wash twice with ethanol, and wash three times with ether, then dissolve the resulting solid in methanol, and evaporate the upper clear solution to dryness under reduced pressure to obtain the product (3.38g). : 95%.
[0237] Ph 3 P + CF 2 CO 2 - : 1 H NMR (300MHz, MeOD) δ7.89–7.61 (m, 15H), 19 F NMR (282MHz, CDCl 3 ) δ - 91.47 (d, 2F).
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 provides a synthesis method of a novel novel difluoromethylene phosphate salt, and an application of the novel difluoromethylene phosphate salt. The above compound has a structure represented by formula A; and in the formula A, all substituents are defined as in the specification. The invention also provides a difluorocarbene generation method and a difluoroolefination method. The compound of the formula A is used in the introduction of difluoro substituted alkyl group or a difluoro substituted alkenyl group into a molecule in the synthesis as a difluororeagent and difluoroolefination agent. A reaction using the difluoromethylene phosphate salt as a reagent has the advantages of mild conditions, high yield and wide application values.
Description
technical field [0001] The present invention relates to the field of organic synthesis. Specifically, the present invention provides a novel difluoromethylene phosphonium internal salt and its synthesis method, as well as the application of the compound in the production of difluorocarbene and difluoroalkenylation reactions, etc. . Background technique [0002] The introduction of fluorine atoms into the compound can greatly change the biological activity and physical properties of the compound, leading to the production of a series of drugs and new materials. Therefore, in the field of compound synthesis, it is necessary to find a method for efficiently introducing fluorine atoms into compound molecules, and it is a relatively important method to introduce fluorine atoms through difluorocarbene as an active intermediate. A series of compounds with difluoro substituents synthesized from difluorocarbene have great applications in industries such as medicine, pesticides, mate...
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