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Method for preparing toluene benzyl phenyl substituted compound

A technology of phenyl substitution and tolyl benzylic position is applied in the field of preparation of tolyl benzylic phenyl substituted compounds, which can solve problems such as difficulty in product purification, and achieve the effects of easy product purification, large-scale industrial production, and low production difficulty.

Inactive Publication Date: 2018-02-09
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The present invention aims at the problems that special photoreactors and photosensitive catalysts need to be used in the preparation reactions of diphenylmethane and diphenhydramine; and a large amount of phosphine ligands or nitrogen ligands need to be added, resulting in extremely difficult product purification, and provides A preparation method of a toluene benzylic phenyl substituted compound is provided, which can be used to prepare diphenylmethane and diphenhydramine, and overcome at least one of the above-mentioned problems

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] A preparation method of diphenylmethane comprises adding 1 mol of toluene, 1 mol of phenylboronic acid, 4 mol of di-tert-butyl peroxide (DTBP), 0.05 mol of nickel acetylacetonate in a 100 mL there-necked flask, 110 After reacting at ℃ for 24 hours, the liquid phase was removed by vacuum distillation, and the residue was purified by column chromatography to obtain 0.95 mol of diphenylmethane.

Embodiment 2

[0023] A preparation method of diphenylmethane, comprising adding 1 mol of toluene, 1 mol of phenylboronic acid, 2 mol of di-tert-butyl peroxide (DTBP), 0.02 mol of nickel acetylacetonate in a 100 mL three-necked flask, at 70°C After reacting for 48 hours, the liquid phase was removed by distillation under reduced pressure, and the residue was purified by column chromatography to obtain 0.94 mol of diphenylmethane.

Embodiment 3

[0025] A preparation method of diphenylmethane comprises adding 1 mol of toluene, 1 mol of phenylboronic acid, 5.94 mol of di-tert-butyl peroxide (DTBP), 0.06 mol of nickel acetylacetonate in a 100 mL there-necked flask, 120 The reaction was carried out at ℃ for 12 hours, the liquid phase was removed by vacuum distillation, and the residue was purified by column chromatography to obtain 0.97 mol of diphenylmethane.

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PUM

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Abstract

In order to solve the deficiencies in the prior art, the present invention provides a method for preparing a toluene benzylic phenyl substituted compound, the method first adds a reaction substrate and an attacking reagent in a reaction vessel, and mixes; then, a catalyst is added to the above-mentioned mixture, and mix uniformly; then, react the above-mentioned homogeneously mixed substance at 70-110° C. for 12-48 hours; finally, remove the solvent and purify the product to obtain the benzylic phenyl substituted product of toluene; the reaction substrate is: A compound containing a phenyl group and at least one alpha hydrogen connected to the phenyl group; the attacking reagent is: phenylboronic acid. The catalyst is a mixture of di-tert-butyl peroxide and nickel acetylacetonate. Adopting the synthetic method of the present invention to synthesize 2kg of diphenhydramine hydrochloride can save the cost of 150,000 yuan.

Description

technical field [0001] The invention belongs to the technical field of chemistry and synthesis, and in particular relates to a preparation method of a toluene benzylic phenyl-substituted compound. Background technique [0002] The C-H bond is the simplest and most common functional group in organic compounds. The chemical synthesis based on the C-H bond activation strategy can simplify raw materials, reduce waste, shorten the reaction route, and realize the target product that is difficult to synthesize by conventional methods. It is the most economical, concise and efficient One of the synthetic pathways, especially of great value in the synthesis of natural products and drug synthesis. Diphenylmethane is an important pharmaceutical and pesticide intermediate, which has broad application prospects in the fields of medicine and pesticides. Many compounds containing diphenylmethane structural units have antibacterial, antitumor, anti-motion sickness and antiemetic effects. D...

Claims

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Application Information

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IPC IPC(8): C07C2/88C07C15/16C07C213/08C07C217/10
CPCC07C2/88C07C213/08C07C15/16C07C217/10
Inventor 周翠兰谭才彪彭翠英李素云向宇燕
Owner NANHUA UNIV