Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A kind of aromatic ring ortho iodoalkanone and its synthesis method and application

A synthetic method and technology of iodoalkanone, which is applied in the field of aromatic ring ortho-iodoalkanone and its synthesis, can solve the problems that cannot be synthesized by intermediates, difficult to stop iodo reaction, difficult iodo synthesis, etc., to achieve Safe and easy to operate, high synthetic yield, suitable for industrial production

Active Publication Date: 2021-07-20
LANZHOU UNIVERSITY
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the iodination reaction on the aromatic ring is affected by the electrical and steric hindrance of the aromatic ring substituent, which makes the synthesis of aromatic ring selective iodination difficult.
Researchers in this field have conducted a large number of experiments and confirmed that functional groups can induce selective aromatic ring iodination reactions, but in the actual operation process, there are still many problems. The most important problem is that the iodination reaction is difficult to stop. In the single-iodination stage, the final product is multi-iodination products of aromatic rings, which cannot be used as intermediates for synthesis

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
  • A kind of aromatic ring ortho iodoalkanone and its synthesis method and application
  • A kind of aromatic ring ortho iodoalkanone and its synthesis method and application
  • A kind of aromatic ring ortho iodoalkanone and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Using 2-phenylcyclohexanone as raw material

[0027]

[0028] In the 10mL reaction tube, add 2-phenylcyclohexanone (34.8mg, 0.2mmol), PIDA (96.6mg, 0.3mmol) and I 2 (50.8mg, 0.2mmol), then add 1.0mL nitromethane, react at room temperature for 2.5h. After the reaction of the raw materials is complete, add a saturated aqueous solution of sodium thiosulfate to the system to quench the remaining oxidant, extract with DCM (5mL*3), wash with water (5mL*3), wash with saturated brine (5mL*2), and perform column chromatography directly (petroleum ether / ethyl acetate=30:1). A colorless liquid (43.2 mg, yield 72%) was finally obtained.

[0029] The product detection data are as follows:

[0030] 1 H NMR (400MHz, CDCl 3 ): δ7.84(dd, J=7.9Hz, J=1.2Hz, 1H), 7.34(td, J=7.5Hz, J=1.2Hz, 1H), 7.17(dd, J=7.8Hz, J=1.7 Hz, 1H), 6.95(td, J=7.8Hz, J=1.7Hz, 1H), 3.99(dd, J=12.3Hz, J=5.2Hz, 1H), 2.57-2.54(m, 2H), 2.31- 2.27(m, 1H), 2.22-2.19(m, 1H), 2.06-2.03(m, 1H), 1.97-1.81(m, 3H);...

Embodiment 2

[0032] Using 2-phenylcyclohexanone as raw material

[0033]

[0034] 2-Phenylcyclohexanone (34.8mg, 0.2mmol, PIFA (129mg, 0.3mmol) and I2 (50.8mg, 0.2mmol) were sequentially added into a 10mL reaction tube, and then 1.0mL HFIP was added, and reacted at room temperature for 7h. The reaction of the raw materials was complete, adding a saturated aqueous solution of sodium thiosulfate to the system to quench the remaining oxidant, extracting with DCM (5mL*3), washing with water (5mL*3), washing with saturated brine (5mL*2), and directly performing column chromatography ( Petroleum ether / ethyl acetate=30:1).A colorless liquid (46.8 mg, yield 78%) was finally obtained.

[0035] The spectral data of the product are the same as in Example 1.

Embodiment 3

[0037] Using 2-phenylcyclohexanone as raw material

[0038]

[0039] 2-Phenylcyclohexanone (34.8mg, 0.2mmol), IBX (84mg, 0.3mmol)) and I2 (50.8mg, 0.2mmol) were sequentially added to a 10mL reaction tube, and then 1.0mL HFIP was added, and reacted at room temperature for 4d . After the raw material completely disappeared, add a saturated aqueous solution of sodium thiosulfate to the system to quench the remaining oxidant, extract with DCM (5mL*3), wash with water (5mL*3), wash with saturated brine (5mL*2), and perform column chromatography directly (petroleum ether / ethyl acetate=30:1). A colorless liquid (46.2 mg, yield 77%) was finally obtained.

[0040] The spectral data of the product are the same as in Example 1.

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

No PUM Login to View More

Abstract

The invention discloses an aromatic ring ortho-iodoalkanone and its synthesis method and application. The structural formula of the aromatic ring ortho-iodoalkanone is as follows: A is an alkyl group or a 5-12-membered ring, R is an alkyl group, Halogen, alkoxy or aryl; R' is hydrogen, alkyl, alkoxy, aryl, substituted aryl or condensed aromatic ring, the synthesis steps include: in the presence of an oxidizing agent, react with an iodinating reagent to obtain the obtained The above-mentioned aromatic ring ortho-iodoalkanone. The invention uses cheap hypervalent iodine reagent as oxidant, can economically and efficiently synthesize aromatic ring ortho iodoalkanone, has simple, safe and easy-to-operate reaction process, high synthesis yield, and is suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of synthesis of organic intermediates, and in particular relates to an aromatic ring ortho iodoalkanone and its synthesis method and application. Background technique [0002] As an important class of organic synthesis intermediates, aryl iodide compounds are widely used in the synthesis of natural organic compounds and pharmaceutical active molecules. However, the iodination reaction on the aromatic ring is affected by the electrical and steric hindrance of the aromatic ring substituent, which makes the synthesis of the selective iodolation of the aromatic ring difficult. Researchers in this field have conducted a large number of experiments and confirmed that functional groups can induce selective aromatic ring iodination reactions. However, in the actual operation process of researchers, there are still many problems. The most important problem is that the iodination reaction is difficult to stop. In the single-io...

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
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07B39/00C07C45/63C07C49/697C07C49/753C07C49/813C07C49/84C07C49/233C07C49/255C07D317/72
CPCC07B39/00C07C49/233C07C49/255C07C49/697C07C49/753C07C49/813C07C49/84C07D317/72C07C2601/08C07C2601/14C07C2601/18C07C2601/20C07C2602/10
Inventor 张辅民卞红丽唐世忠
Owner LANZHOU UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products