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Application method of Grignard reaction

A technology of Grignard reaction and application method, which is applied in the new application field of Grignard reaction, and can solve problems such as coupling side reactions, explosion, and flushing that are prone to occur

Inactive Publication Date: 2021-03-30
DALIAN QIKAI MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is precisely because of the strong activity of Grignard reagents that the reaction or storage of Grignard reagents is prone to flushing, serious or even explosion hazards, and coupling side reactions are also prone to occur. The higher the concentration of Grignard reagents in the system, the The probability of the above reaction is greater. In addition, in the preparation of Grignard reagents, tetrahydrofuran, the main solvent, is more expensive and difficult to recycle and apply mechanically. In addition, the amount of solvent used in the Grignard reaction is large, and the product volume ratio All of the above have greatly hindered the application of Grignard reaction in industrialization

Method used

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  • Application method of Grignard reaction
  • Application method of Grignard reaction
  • Application method of Grignard reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] Traditional two-step method:

[0029] 1, the preparation of isopropylmagnesium bromide:

[0030] In a 500mL four-necked bottle equipped with a thermometer, a condenser and a dropping funnel, add 10 grams of magnesium chips (0.42mol) and 150mL of anhydrous ether, respectively, and protect it with nitrogen, and add 50 grams (0.4mol) of bromine into the dropping funnel. A mixture of isopropane and 50 mL of anhydrous ether.

[0031] First add 3-4mL of the mixed solution into the four-neck flask, and the reaction starts to boil slightly after a few minutes. The reaction was intense at the beginning, and after it was relieved, the stirring was started, and the remaining mixed solution of ethyl bromide and ether was added dropwise, and the rate of addition was controlled so that the solution in the bottle was in a slightly boiling state. After the addition, heat and reflux in a warm water bath for 15 minutes, then cool down for later use.

[0032] 2. Preparation...

Embodiment 2

[0041]

[0042] Traditional two-step method:

[0043] Preparation of 3,4,5-trifluorophenylmagnesium bromide:

[0044] Add 42mmol (10.08g) of magnesium chips into a 500mL four-neck flask, add 2 grains of iodine, then add 200mL of anhydrous 2-methyltetrahydrofuran, heat the temperature to 50°C, and then let it cool down to 40°C naturally , and then drop 4-5mL of a mixed solution consisting of 84.4 grams (0.4mol) of 3,4,5-trifluorobromobenzene and 50mL of 2-methyltetrahydrofuran to initiate a Grignard reaction, and the temperature will rise rapidly after the reaction is initiated. Cool the temperature down to 10-15°C in an ice-water bath, then slowly add the remaining 3,4,5-trifluorobromobenzene mixed solution dropwise for about 2.0-3.0 hours, and react at room temperature for 8 hours after the dropwise addition.

[0045] Preparation of 3,4,5-trifluorophenylboronic acid:

[0046] Weigh 0.42mol (44g) of trimethyl borate, add it to a 1000mL four-neck flask, then add 200mL 2-meth...

Embodiment 3

[0051]

[0052] Traditional two-step method:

[0053] 1. Preparation of phenylmagnesium bromide:

[0054] Add 42mmol (10.08g) of magnesium chips into a 500mL four-necked flask, add 2 grains of iodine, and then add 200mL of anhydrous tetrahydrofuran, heat the temperature to 50°C, then let it cool down to 40°C naturally, and then add dropwise 4-5mL of a mixture consisting of 63 grams of bromobenzene (0.4mol) and 50mL of tetrahydrofuran will initiate a Grignard reaction, and the temperature will rise rapidly after the reaction is initiated. Use an ice-water bath to lower the temperature to 10-15°C, and then slowly add The remaining bromobenzene mixed solution, the dropwise addition time is about 2.0-3.0h, after the dropwise addition is completed, react at room temperature for 8h.

[0055] 2. Preparation of 2-phenyl-4,6-dichloro-1,3,5-triazine:

[0056] Weigh 0.42mol (78g) of cyanuric chloride, add it to a 1000mL four-neck flask, add 200mL tetrahydrofuran to dilute, put the f...

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Abstract

The invention discloses an application method of a Grignard reaction, belonging to the technical field of organic synthesis. According to the invention, a two-way dropwise adding mode is adopted, andpreparation of a Grignard reagent and a Grignard reaction are carried out at the same time; as the Grignard reaction is carried out while the Grignard reagent is prepared, the concentration of the Grignard reagent in a reaction system is reduced, and coupling side reactions are reduced; the use amount of a solvent in the reaction system is reduced, the accumulation rate of raw materials is increased, yield is increased and cost is reduced; and meanwhile, in the reaction system, the activity of the Grignard reagent in the system is reduced due to the reduction of the concentration of the Grignard reagent, so an explosion risk caused by over-high concentration of the Grignard reagent during storage and reaction of the Grignard reagent is avoided.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to a new application method of Grignard reaction. Background technique [0002] The Grignard reaction was invented in 1989 by Victor Grignard, who was a graduate student at the University of Lyons in France. In 1912, he and Paul Sabatier, a French scholar who invented the catalytic hydrogenation reaction of platinum and palladium metals, won the Nobel Prize in Chemistry that year. prize. For more than one hundred years, the Grignard reaction has been the most commonly used organic chemical reaction, especially the name reaction, and it is one of the chemical reactions with industrial production value. [0003] The Grignard reaction is mainly used to construct the combination of carbon-carbon bonds, and the main functional groups that can chemically react with it are carbonyl, ester and halide. In addition, epoxy groups, cyano groups, lactones, acid anhydrides and diester...

Claims

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Application Information

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IPC IPC(8): C07B49/00C07C29/40C07C31/125C07C33/34C07D251/20C07F5/02
CPCC07B49/00C07C29/40C07F5/025C07D251/20C07C2601/02
Inventor 杨永正张洪学姜殿宝
Owner DALIAN QIKAI MEDICAL TECH
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