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Synthesis method of (E)-methyl ester 3-(3,5-difluoro-4-formyl phenyl)acrylic acid

The technology of a formyl phenyl group and a synthesis method, which is applied in the synthesis field of -methyl 3-acrylic acid, can solve the problems of high cost, unsuitability for mass production, unfriendly environment and the like, and achieves high safety, good application prospect, Environmentally friendly effect

Pending Publication Date: 2021-07-13
成都道合尔医药技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In summary, the current methods for synthesizing (E)-methyl ester 3-(3,5-difluoro-4-formylphenyl)acrylic acid are costly, environmentally unfriendly, and not suitable for mass production

Method used

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  • Synthesis method of (E)-methyl ester 3-(3,5-difluoro-4-formyl phenyl)acrylic acid
  • Synthesis method of (E)-methyl ester 3-(3,5-difluoro-4-formyl phenyl)acrylic acid
  • Synthesis method of (E)-methyl ester 3-(3,5-difluoro-4-formyl phenyl)acrylic acid

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Embodiment 1

[0048] Example 1, the synthesis method of (E)-methyl ester 3-(3,5-difluoro-4-formylphenyl)acrylic acid of the present invention (1) Preparation of compound 2a-c

[0049] Preparation of compound 2a:

[0050]

[0051]To a suspension of compound 1 (180 g, 0.814 mol) in methanol (900 mL) were added trimethyl orthoformate (112.4 g, 1.059 mol) and ammonium chloride (2.2 g, 0.041 mol). React at 45-55°C for 20 hours. Concentrate under reduced pressure, add MTBE (600 mL), wash with saturated sodium bicarbonate (150 mL), wash with saturated sodium chloride (150 mL), and concentrate under reduced pressure to obtain a crude product. The crude product was purified by distillation to obtain 201 g of light yellow liquid with a yield of 92.4%.

[0052] Preparation of compound 2b:

[0053]

[0054] To a suspension of compound 1 (100 g, 0.452 mol) in ethanol (500 mL) was added triethyl orthoformate (95 g, 0.641 mol) and ammonium chloride (1.3 g, 0.024 mol). React at 45-55°C for 20 hou...

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Abstract

The invention provides a synthesis method of (E)-methyl ester 3-(3,5-difluoro-4-formyl phenyl)acrylic acid, and relates to the field of organic synthesis. The method comprises the following steps: (1) aldehyde group protection: reacting a compound 1, ammonium chloride and alcohol to obtain a compound 2, wherein the alcohol is selected from monohydric alcohol or dihydric alcohol; (2) introducing formyl: reacting the compound 2 serving as a raw material with an organic metal reagent in an organic solvent, and then adding N,N-dimethylformamide for reaction to obtain a compound 3; (3) Wittig-Horner reaction: adding alkali and a compound containing a phosphonate group into the compound 3, and reacting to obtain a compound 4; and (4) deprotection reaction: adding a compound containing a sulfonic acid group and water into the compound 4, and reacting to obtain the product. The synthesis method does not use a noble metal catalyst, so that the cost is obviously reduced; and the product prepared by the synthesis method is high in yield, high in purity, environment-friendly, high in safety and suitable for industrial production, and has a good application prospect.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing (E)-methyl ester 3-(3,5-difluoro-4-formylphenyl)acrylic acid. Background technique [0002] After long-term basic research and clinical observation, many diseases such as breast cancer, ovarian cancer, osteoporosis, schizophrenia and Alzheimer's disease are related to the aberration of estrogen signaling pathway. Estrogen is a steroid hormone secreted by the endocrine system, which plays an important role in the reproductive system, bone tissue, cardiovascular system, immune system and central nervous system. The estrogen signaling system plays an important regulatory role in the process of cell growth, differentiation and apoptosis. The occurrence and development of certain tumors, such as breast cancer, ovarian cancer and uterine cancer, have the most direct relationship with estrogen. Currently, chemotherapy for breast cancer uses an anti-estrogen, ...

Claims

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Application Information

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IPC IPC(8): C07C67/313C07C69/738
CPCC07C67/313C07C67/343C07D317/26C07C45/455C07C41/56C07C69/738C07C69/73C07C47/575C07C43/313
Inventor 魏庚辉宁兆伦陈国龙黄湘川
Owner 成都道合尔医药技术有限公司
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