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Preparation of 4-bromo-2-(4 '-ethoxy-benzyl)-1-chlorobenzene

An ethoxy and benzyl technology, applied in the field of compound synthesis, can solve the problems of short steps, good selectivity and high yield

Inactive Publication Date: 2021-03-16
WISDOM PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] This method step is short, and selectivity is good, and yield is also high, and weak point is the use of a large amount of acid chlorination reagents and the generation of acid waste in acyl chloride reaction, and the use of aluminum trichloride and acid waste water in Friedel-Crafts reaction Problems, do not meet the requirements of green production, and greatly increase the corrosion resistance requirements and maintenance costs of production equipment
[0012] Therefore, the existing acylation method of synthesizing 4-bromo-2-(4'-ethoxy-benzyl)-1-chlorobenzene has the use of acidic materials and acid waste gas (hydrogen chloride, etc.), acid waste water (trichloride, etc.) aluminum, etc.); the alkylation method has long steps, poor selectivity and reaction safety problems, which are very troublesome for industrial scale-up production

Method used

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  • Preparation of 4-bromo-2-(4 '-ethoxy-benzyl)-1-chlorobenzene
  • Preparation of 4-bromo-2-(4 '-ethoxy-benzyl)-1-chlorobenzene
  • Preparation of 4-bromo-2-(4 '-ethoxy-benzyl)-1-chlorobenzene

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Embodiment 1

[0018] Embodiment one: the synthesis of 4-bromo-2-(4'-ethoxy-benzyl)-1-chlorobenzene

[0019] Add trifluoroacetic anhydride (84.0g, 400mmol), phenetole (14.7g, 120mmol), boron trifluoride etherate (1.42g, 10mmol) successively into a 250mL four-necked bottle, and add 2-chloro-5- Bromo-benzoic acid (23.5g, 100mmol) was heated to 30±5°C with stirring for 6 hours to obtain a dark brown solution. After cooling down to room temperature, triethylsilane (34.9 g, 300 mmol) was added, and the temperature was raised to 55-60° C. for 18 hours. After cooling down, concentrate under reduced pressure to remove the low-boiling point solvent. Add dichloromethane (150 mL) and saturated sodium bicarbonate solution (60 mL) to the residue to wash and separate the layers. The collected organic layer is washed twice with water (60 mL×2) and then concentrated. The residue was recrystallized by adding ethanol, filtered, and air-dried at 40°C to obtain the white title compound (24.3 g, yield 74.5%).

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Abstract

The invention aims to provide a method for synthesizing 4-bromo-2-(4 '-ethoxy-benzyl)-1-chlorobenzene, which has shorter steps and is greener, and provides a more effective synthesis strategy for production of key intermediates of SGLT-2 inhibitor drugs such as dapagliflozin, sotagliflozin, ertugliflozin and the like. The method comprises the following steps: selecting 2-chlorine-5-bromobenzoic acid and phenethyl ether, completing a direct acylation reaction in the presence of trifluoroacetic anhydride by taking boron trifluoride diethyl ether as a catalyst, adding triethylsilane without treatment, and carrying out a one-pot reaction to obtain the target compound 4-bromo-2-(4 '-ethoxy-benzyl)-1-chlorobenzene.

Description

technical field [0001] The invention belongs to the field of compound synthesis methods, in particular to the synthesis of compound 4-bromo-2-(4'-ethoxy-benzyl)-1-chlorobenzene. Background technique [0002] SGLT-2 protein exists in the lumen of human glomerular epithelial cells, under its action, the glucose filtered through the renal tubules is reabsorbed as high as 90%, and the biological effect of SGLT-2 protein can be inhibited to reduce the blood sugar purpose. As a new type of hypoglycemic drug, the unique hypoglycemic mechanism of SGLT-2 inhibitors has nothing to do with insulin, and is a new target of insulin-independent hypoglycemic drugs, and the risk of hypoglycemia is very low. Compared with other hypoglycemic drugs, its mechanism of action is novel, and it opens a new way for excreting excess glucose in the blood. SGLT-2 inhibitors have good performance in reducing blood sugar, cardiovascular protection, kidney protection, etc., and may even be used in combin...

Claims

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Application Information

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IPC IPC(8): C07C41/30C07C43/225B01J31/22B01J31/04
CPCC07C41/30B01J31/2208B01J31/04C07C43/225C07C45/46C07C41/18C07C49/84
Inventor 胡林徐涛邱小龙李小跃左智伟刘文博储玲玲袁希萌邹平
Owner WISDOM PHARM CO LTD
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