Preparation method for aromatic nitrile compound
A compound, aromatic nitrile technology, applied in the field of preparation of aromatic nitrile compounds, can solve the problems of poor functional group compatibility, small range of reaction substrates, harsh reaction conditions, etc., to achieve wide substrate universality and easy purification of products , the effect of simple substrate
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Example Embodiment
[0028] Example 1
[0029] Synthesis of p-methoxybenzonitrile
[0030] Under nitrogen protection, 61 mg (ie 0.5 mmol) of p-methoxytoluene, 103 mg (ie 1.0 mmol) of nitroso-tert-butyl ester, and 25 mg (0.15 mmol) of N-hydroxyphthalimide were successively added to the microwave tube. Amine and 5.6 mg of palladium acetate (ie, 0.025 mmol) were heated to 70° C. in 0.5 mL of acetonitrile to react for 24 hours. The reaction system was cooled to room temperature and diluted with 2 mL of dichloromethane. The mixture was filtered and concentrated. The reaction solution is purified by eluent column chromatography with petroleum ether to obtain p-methoxybenzonitrile, and its structure is shown in the following formula:
[0031]
[0032] The compound is a white solid with a yield of 84%, and its NMR data are as follows:
[0033] 1 HNMR(CDCl3,400MHz):δ=7.59(d,J=8.8Hz,2H),6.97(d,J=8.8Hz,2H),3.86(s,3H); 13 CNMR(CDCl3, 100MHz): δ=162.8, 133.9, 119.2, 114.7, 103.9, 55.5.
Example Embodiment
[0034] Example 2
[0035] Synthesis of m-methoxybenzonitrile
[0036] Under nitrogen protection, 61 mg (ie 0.5 mmol) of m-methoxytoluene, 103 mg (ie 1.0 mmol) of nitroso-tert-butyl ester, and 25 mg (0.15 mmol) of N-hydroxyphthalimide were successively added to the microwave tube. Amine and 5.6 mg of palladium acetate (ie, 0.025 mmol) were heated to 70° C. in 0.5 mL of acetonitrile to react for 24 hours. The reaction system was cooled to room temperature and diluted with 2 mL of dichloromethane. The mixture was filtered and concentrated. The reaction solution is purified by eluent column chromatography with petroleum ether to obtain m-methoxybenzonitrile, and its structure is shown in the following formula:
[0037]
[0038] The compound is a colorless oily liquid with a yield of 81%, and the data are as follows:
[0039] 1 H NMR (CDCl 3 ,400MHz):δ=7.39-7.35(m,1H),7.28-7.23(m,1H),7.14-7.13(m,2H),3.83(s,3H); 13 C NMR (CDCl 3,100MHz):δ=159.5,130.2,124.4,119.2,118.6,116.8...
Example Embodiment
[0040] Example 3
[0041] Synthesis of o-methoxy tert-butyl ester
[0042] Under nitrogen protection, 61 mg (ie 0.5 mmol) of o-methoxytoluene, 154 mg (ie 1.5 mmol) of nitroso-tert-butyl ester, and 25 mg (0.15 mmol) of N-hydroxyphthalimide were successively added to the microwave tube. Amine and 5.6 mg of palladium acetate (ie, 0.025 mmol) were heated to 70° C. in 0.5 mL of acetonitrile to react for 24 hours. The reaction system was cooled to room temperature and diluted with 2 mL of dichloromethane. The mixture was filtered and concentrated. The reaction solution is purified by eluent column chromatography with petroleum ether to obtain o-methoxybenzonitrile, and its structure is shown in the following formula:
[0043]
[0044] The compound is a yellow liquid with a yield of 92%, and the data are as follows:
[0045] 1 H NMR (CDCl 3 ,400MHz):δ=7.57-7.53(m,2H),7.03-6.98(m,2H),3.93(s,3H); 13 C NMR (CDCl 3 ,100MHz):δ=161.0,134.3,133.5,120.6,116.4,111.2,101.5,55.8.
PUM
Abstract
Description
Claims
Application Information
- R&D Engineer
- R&D Manager
- IP Professional
- Industry Leading Data Capabilities
- Powerful AI technology
- Patent DNA Extraction
Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.
© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap