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A kind of synthetic method for preparing 5-bromo-2-chloro-4'-ethoxydiphenylmethane

A technology for the synthesis of ethoxydiphenylmethane, which is applied in the direction of condensation preparation of carbonyl compounds, ether preparation, halogenated hydrocarbon preparation, etc., can solve the problems of high cost of raw materials, many auxiliary materials and solvents, which are not conducive to production, and achieve Easy to obtain, low equipment requirements, and low cost effects

Active Publication Date: 2022-04-05
SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Another example: application number CN201710566635.1, application publication number CN107311847A patent application for invention, using 4-hydroxybenzaldehyde and bromoethane as raw materials, through substitution, condensation, diazotization, Sandmeyer, reduction synthesis, although the raw materials It is a common raw material, but the auxiliary materials and solvents used are many and cumbersome, and the yield is low
In addition, there is also a technical proposal to use 5-bromo-2-chlorobenzoic acid as the starting raw material, which is obtained through acyl chloride, Friedel-Crafts acylation and reduction, wherein the raw material cost is high and the yield is not high, which is not conducive to production

Method used

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  • A kind of synthetic method for preparing 5-bromo-2-chloro-4'-ethoxydiphenylmethane
  • A kind of synthetic method for preparing 5-bromo-2-chloro-4'-ethoxydiphenylmethane

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preparation example Construction

[0032] Such as figure 1 Shown, during concrete implementation, the synthetic method that the present invention prepares 5-bromo-2-chloro-4'-ethoxydiphenylmethane comprises:

[0033] The first step, get o-chlorobenzoic acid, first add solvent and catalyzer, then drip acid chloride reagent, obtain o-chlorobenzoyl chloride ( figure 1 Compound I); Wherein, the weight ratio of o-chlorobenzoic acid and solvent is 1:4.0-6.0, the weight ratio of o-chlorobenzoic acid and catalyst is 1:0.003-0.006, the molar ratio of o-chlorobenzoic acid and acyl chloride reagent It is 1:1.05-1.15.

[0034] Specifically, after adding solvent and catalyst, stir evenly, add acid chloride reagent dropwise at 0°C-10°C; react at 20°C-30°C for 2-4 hours; depressurize at 40°C-70°C after the reaction The solvent is recovered by distillation; the solvent is dichloroethane, toluene or dichloromethane (preferably dichloromethane); the catalyst is pyridine or DMF (preferably pyridine); the acyl chloride reagent i...

Embodiment 1

[0045] This embodiment is for the preparation of o-chlorobenzoyl chloride ( figure 1 Compound I).

[0046] The basic process of this embodiment is the first step of the technical solution of the present invention during specific implementation.

[0047] Some specific parameters of this embodiment are as follows:

[0048] Add 156.0g (1.0mol) of o-chlorobenzoic acid, 800g of dichloromethane, and 0.8g of DMF into a 2000ml four-necked reaction flask, start stirring, cool down to 10°C, add 139.7g (1.1mol) of oxalyl chloride dropwise, and drop to room temperature (20°C-30°C) react for 3 hours (up to 0.2% of raw materials detected by HPLC), evaporate the solvent to obtain an oily substance, mainly o-chlorobenzoyl chloride, and a small amount of oxalyl chloride; the oily substance is detected by HPLC The purity is 99.0%. The purity is calculated according to the HPLC area normalization method, and the solvent peak is deducted during the calculation. Simultaneously, because oxalyl ch...

Embodiment 2

[0050] This embodiment is for the preparation of 2-chloro-4'-iodobenzophenone ( figure 1 compound II).

[0051] The basic process of this embodiment is the second step of the technical solution of the present invention during specific implementation.

[0052] Some specific parameters of this embodiment are as follows:

[0053] Add the oil obtained in Example 1 (containing 172.4 g (0.985 mol) of o-chlorobenzoyl chloride) and 350.0 g of dichloromethane into a 1000 ml four-necked reaction flask, protect with nitrogen, cool down to 0°C, and add aluminum trichloride in batches 144.6g (1.08mol), add 205.0g (1.00mol) of iodobenzene dropwise, react at 0°C-5°C for 2 hours (until the detection of raw materials by HPLC<0.3%), pour into ice water after the end (control the addition temperature <20°C) , Since aluminum trichloride is poured into water, it will exotherm violently, and if the temperature is too high, the impurity content will be too high, so the temperature should be contro...

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Abstract

The invention relates to a synthesis method for preparing 5-bromo-2-chloro-4'-ethoxydiphenylmethane. First, o-chlorobenzoic acid is chlorinated to produce o-chlorobenzoyl chloride, and then Friedel-Crafts acylation to produce 2‑Chloro‑4'‑iodobenzophenone, further brominated to 5‑Bromo‑2‑Chloro‑4'‑iodobenzophenone, which was reduced to 5‑Bromo‑2‑Chloro‑4' ‑Iododiphenylmethane, which eventually undergoes a substitution reaction to produce 5‑bromo‑2‑chloro‑4'‑ethoxydiphenylmethane. The method of the invention has a streamlined route, high purity of the obtained product, the raw materials and auxiliary materials used are common compounds, low toxicity solvents are used and can be recycled and reused, no phosphorus-containing waste water is produced, the safety is high, the environment is friendly, the cost is low, and the equipment is The requirements are not high, and it is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis method for preparing 5-bromo-2-chloro-4'-ethoxydiphenylmethane, which belongs to the technical field of preparation of pharmaceutical intermediates. Background technique [0002] As far as the applicant knows, Dapagliflozin is a new type of anti-diabetic drug jointly developed by Bristol-Myers Squibb and AstraZeneca, which was approved for marketing by the European Medicines Agency (EMA) on November 12, 2012. It is the first SGLT2 inhibitor approved for marketing for the treatment of type 2 diabetes. It can be used as an important choice in diabetes drug treatment and is suitable for adults with type 2 diabetes as an auxiliary diet and exercise to improve blood sugar control. The U.S. Food and Drug Administration (FDA) announced on January 8, 2014 that it approved dapagliflozin for the treatment of type 2 diabetes. Dapagliflozin works by inhibiting sodium-glucose transporter 2 (SGLT2), a protein in the kidney that ...

Claims

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Application Information

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IPC IPC(8): C07C51/60C07C63/70C07C45/45C07C45/46C07C49/813C07C17/35C07C25/18C07C41/16C07C43/225
CPCC07C51/60C07C45/455C07C45/46C07C17/35C07C41/16C07C63/70C07C49/813C07C25/18C07C43/225
Inventor 高鹏沈冰良韦伟张庆战
Owner SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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