Unlock instant, AI-driven research and patent intelligence for your innovation.
Synthesis method for thiophene ring/furan ring-heteroaromatic ring structure
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 alkyl technology, applied in the field of chemistry, can solve problems such as poor compatibility of functional groups and lengthy reaction steps
Active Publication Date: 2013-04-10
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
View PDF1 Cites 3 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, these methods usually have disadvantages such as lengthy reaction steps, poor functional group compatibility, and some reactions require the use of some highly toxic tin 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
[0049]The present invention provides a method for preparing a thiophene ring / furan ring and its derivatives-heteroaromatic ring building blocks. Preferably, the method comprises the steps of:
[0050] In an inertsolvent, at a certain temperature (such as 40°C-140°C; preferably 60-100°C), using palladium salt as a catalyst, in the presence of an oxidizing agent, the compound of formula A (ie thiophene ring or furan ring or Its derivative) reacts with the compound of formula B (ie heteroaromatic ring compound) for a period of time (such as 1-20 hours or 5-10 hours, etc.), thereby forming the compound of formula C (ie thiophene ring / furan ring and its derivatives -heteroaromatic ring building blocks);
[0051]
[0052] In various forms, R 1 , R 2 , R 3 , R' 1 , R' 2 , R' 3 , X, Y are defined as mentioned above.
[0053] Wherein, the compound of formula A is preferably a compound selected from the following group:
[0054]
[0055] In various forms, R 1 , R 2 , R ...
Embodiment 1
[0075]
[0076] Into a 25 mL reaction tube, add 6.7 mg (10 mol%) of Pd(OAc) 2 , AgOAc (0.9mmol), 2-N,N-dimethylformamidothiophene (0.3mmol, 1 equiv), nitrogen replacement three times and then add 2mL dimethylformamide (DMF), inject 87μL (0.45mmol)2 -Bromo-3-hexylthiophene, 30% yield after stirring at 80 °C for 8 hours.
Embodiment 2
[0078]
[0079] Into a 25 mL reaction tube, add 6.7 mg (10 mol%) of Pd(OAc) 2 , AgOAc (0.9mmol), 2-N,N-dimethylformamidothiophene (0.3mmol, 1 eq), nitrogen replacement three times, adding 2mL dimethylsulfoxide (DMSO), injecting 87μL (0.45mmol)2 -Bromo-3-hexylthiophene, after stirring at 80°C for 8 hours, the target compound was obtained by column separation with a yield of 28%.
[0080] 1 H NMR (300MHz, CDCl 3 )δ7.24(d,J=3.9Hz,1H),7.00(d,J=3.9Hz,1H),6.92(s,1H),3.19(s,6H),2.53(t,J=7.8Hz, 2H),1.57(m,2H),1.32(m,6H),0.89(t,J=6.6Hz,3H). 13 C NMR (75.4MHz, CDCl 3 )δ163.7, 143.1, 140.2, 136.4, 135.7, 130.0, 125.4, 122.9, 108.8, 31.5, 29.5, 29.4, 28.8, 22.5, 14.0.m.p.54°C.IR (thin film method): v max 3068,1610cm -1 .MS(EI):m / z(%)401(M + ),399(M + ), 274(100), 243, 171.HRMS: Calculated for (theoretical value): C 17 h 22 NOS 2 Br: 399.0326; Found (measured value): 399.0331.
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 discloses a synthesis method for a thiophene ring / furan ring-heteroaromatic ring structure. Specifically, according to the synthesis method provided by the invention, various high-yield thiophene ring / furan ring-heteroaromatic ring building block compounds are prepared from thiophene ring or furan ring or derivatives thereof and heteroaromatic ring compounds in the prescence of palladium salt and oxidant. The synthesis method has the advantages of simple and readily available raw materials, small using amount of catalysts, wide application range of substrates, simplicity and convenience in operation, high reaction efficiency and the like. The prepared thiophene ring / furan ring-heteroaromatic ring building blocks are widely applied in the aspects of photoelectric materials, luminescent agents, solar batteries and the like.
Description
technical field [0001] The present invention belongs to the field of chemistry. Specifically, the present invention relates to a synthesis method of a thiophene ring / furan ring-heteroaryl ring building block. Background technique [0002] Thiophene ring / furan ring-heteroaromatic ring building blocks play a very important role in organic electronic devices (such as organic light-emitting materials, optoelectronic materials, field-effect semiconductors, organic solar cells, etc.). However, in the traditional method of synthesizing thiophene ring / furan ring-heteroaromatic ring building blocks, it is usually prepared from pre-activated arene metal reagents (such as arylboron compounds, aryltin compounds, etc.) and halogenated arenes. (eg, (a) de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. Wiley-VCH, Weinheim, 2004. (b) Cheng, Y.-J.; Yan, S. -H.;Hsu,C.-S.Chem.Rev.2009,109,5868.(c)Carsten,B.;He,F.;Son,H.-J.;Xu,T.;Yu,L . Chem. Rev. 2011, 111, 1...
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