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The preparation method of 5-bromo-2-chloro-4'-ethoxydiphenylmethane

A technology of ethoxydiphenylmethane and ethoxybenzophenone is applied in the preparation of hydrocarbon ammoxidation, the preparation of carbon-based compounds, the preparation of organic compounds, etc., and can solve the problems of highly toxic cyanide, serious pollution and the like, Achieve the effect of high product purity and short synthesis route

Active Publication Date: 2020-11-10
安徽省诚联医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The benzylation of this process route uses AIBN, which will produce highly toxic cyanide during the reaction process and cause serious pollution, such as patent CN104478670

Method used

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  • The preparation method of 5-bromo-2-chloro-4'-ethoxydiphenylmethane
  • The preparation method of 5-bromo-2-chloro-4'-ethoxydiphenylmethane
  • The preparation method of 5-bromo-2-chloro-4'-ethoxydiphenylmethane

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Embodiment Construction

[0023] The present invention will be further described below through the examples, but the examples do not limit the protection scope of the present invention.

[0024] 1, the preparation of 4-ethoxybenzaldehyde

[0025] The reaction chemical formula is:

[0026]

[0027] Get 122kg of 4-hydroxybenzaldehyde, dissolve it in 200kgDMF, 50kg toluene, add potassium carbonate 150kg, at 60°, add dropwise the toluene solution of bromoethane (bromoethane 130kg, toluene 150kg), dropwise in 30 minutes, add dropwise Completed, reacted at 60 ° for 2 hours, after the reaction, filtered to remove potassium bromide and potassium carbonate, recovered the solvent under reduced pressure, added 400kg of water to the residual liquid, extracted with 400kg of ethyl acetate, dried over anhydrous sodium sulfate, filtered, recovered the solvent from the filtrate, and left The product was distilled under reduced pressure to obtain 136.5 kg of a light yellow liquid with a yield of 91%.

[0028] 2, Pr...

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Abstract

The invention provides a preparation method of 5-bromine-2-chlorine-4'-ethyoxyl diphenylmethane. The preparation method comprises the following steps: (1) using 4-hydroxybenzaldehyde and bromoethane as raw materials, a polar solvent as a reaction solvent and inorganic base as a catalyst to react so as to prepare 4-ethoxy-benzaldehyde; (2) using hydroxylamine hydrochloride and 4-hydroxybenzaldehyde as raw materials and a hydroxyl-containing solvent as a reaction solvent to react so as to obtain oxime, and then reacting under the effect of a dehydrating agent so as to generate 4-ethoxyl benzonitrile; (3) using 4-bromaniline and 4-ethoxyl benzonitrile as raw materials, using lewis acid as a catalyst, and performing a Hoesch reaction to generate 5-bromine-2-amino-4'-ethyoxyl benzophenone; (4) performing a diazo-reaction on 5-bromine-2-amino-4'-ethyoxyl benzophenone, and then reacting with cuprous chloride to synthesize 5-bromine-2-chlorine-4'-ethyoxyl benzophenone; and (5) performing a reduction reaction on 5-bromine-2-chlorine-4'-ethyoxyl benzophenone to obtain 5-bromine-2-chlorine-4'-ethyoxyl diphenylmethane. The method is low in cost, low in environment stress and short in synthetic route.

Description

technical field [0001] The invention relates to a preparation method of 5-bromo-2-chloro-4'-ethoxydiphenylmethane. Background technique [0002] Dapagliflozin is a sodium-glucose cotransporter-2 (SGLT2) inhibitor, C-aryl glucoside compound, chemical name: (2S, 3R, 4R, 5S, 6R )-2-[3-(4-ethoxybenzyl)-4-chlorophenyl]-6-hydroxymethyltetrahydro-2H-pyran-3,4,5-triol. Dapagliflozin inhibits the reabsorption of blood sugar by inhibiting renal sodium-glucose cotransporter 2, thereby regulating blood sugar levels in the body; at the same time, it can significantly reduce the level of glycosylated hemoglobin and body weight of patients. Dapagliflozin, jointly developed by Bristol-Myers Squibb and AstraZeneca, is the second SGLT2 inhibitor approved by the US FDA for the treatment of type 2 diabetes. [0003] 5-Bromo-2-chloro-4'-ethoxydiphenylmethane is the key intermediate for the preparation of Dapagliflozin. There are two main synthetic methods. One method is to use 5-bromo-2-chloro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/225C07C41/18C07C45/64C07C47/575C07C253/26C07C255/54C07C221/00C07C225/22C07C45/63C07C49/84
CPCC07C41/18C07C45/63C07C45/64C07C221/00C07C253/26C07C47/575C07C255/54C07C225/22C07C49/84C07C43/225
Inventor 刘辉
Owner 安徽省诚联医药科技有限公司