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Green synthesis method of bromomethylbiphenyl compound

A technology of bromomethylbiphenyl and compounds, which is applied in the field of preparation of bromomethylbiphenyl compounds, can solve the problem of high energy requirements, and achieve the effects of sufficient production capacity, high yield, and good atom economy

Active Publication Date: 2010-02-17
CHINA RESOURCES SAIKE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Secondly, the photoinitiation used in the patent report is a high-pressure or low-pressure mercury lamp. By controlling the temperature, the conversion rate of the reaction can reach 87-92%, and the selectivity can reach 92-95%, but the requirements for equipment and energy are high.

Method used

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  • Green synthesis method of bromomethylbiphenyl compound
  • Green synthesis method of bromomethylbiphenyl compound
  • Green synthesis method of bromomethylbiphenyl compound

Examples

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Effect test

Embodiment 1

[0029] Example 1: Preparation process 1 of 4'-bromomethyl-2-cyanobiphenyl

[0030] In a 2L three-necked flask, add 96.6g (0.50mol) of 4'-methyl-2-cyanobiphenyl (OTBN), 75g of dibromohydantoin, and 300ml of dichloromethane, and control the temperature in a low-temperature bath to 10-20°C. Then react under sunlight for 2 hours, after the reaction is complete. Detection result (HPLC): Br-OTBN 89.2%, Br 2 -OTBN 6.76%, OTBN 4.04%). The reaction solution was washed with 400ml of 5% sodium bicarbonate and 400ml of water, and the organic layer was concentrated and evaporated to dryness to obtain a crude solid, which was then suspended in 200ml of ethyl acetate and washed with stirring. At ~15°C, heat and crystallize for 4 hours, filter, and dry the solid to obtain 115.6 g, the total yield is 85%, and the purity of the obtained solid is greater than 98%.

Embodiment 2

[0031] Embodiment 2: Preparation process 2 of 4'-bromomethyl-2-cyanobiphenyl

[0032] In a 2L three-necked flask, add 96.6g (0.50mol) of 4'-methyl-2-cyanobiphenyl (OTBN), 94g of dibromohydantoin, and 300ml of dichloromethane, and control the temperature in a low-temperature bath to 0-10°C. Then react under light for 4h, and the reaction is complete. Test result (HPLC): Br-OTBN 91.5%, Br 2 -OTBN 5.05%, OTBN 3.45%). The reaction solution was washed with 400ml of 5% sodium bicarbonate and 400ml of water respectively, concentrated and evaporated to dryness to obtain a crude solid, which was then suspended in 200ml of ethyl acetate and washed with stirring. ℃, keep warm and crystallize for 4 hours, filter, and dry the solid to obtain 117.6 g, the total yield is 86.5%, and the purity of the obtained solid is greater than 98.5%.

Embodiment 3

[0033] Example 3: Preparation process 3 of 4'-bromomethyl-2-cyanobiphenyl

[0034] In a 2L three-necked flask, add 96.6g (0.50mol) 4'-methyl-2-cyanobiphenyl (OTBN), 94g dibromohydantoin, 300ml dichloromethane, add 100ml water, and control the temperature to 0 ~10°C, then reacted for 3 hours under light, and the reaction was completed. Detection result (HPLC): Br-OTBN 91.2%, Br 2 -OTBN 5.95%, OTBN 2.85%). The reaction solution was washed with 400ml of 5% sodium bicarbonate and 400ml of water respectively, concentrated and evaporated to dryness to obtain a crude solid, which was then suspended in 200ml of ethyl acetate and washed with stirring. ℃, heat preservation and crystallization for 4 hours, filter, and dry the solid to obtain 116.2 g, the total yield is 85.4%, and the purity of the obtained solid is greater than 98.5%.

[0035] Embodiment 3: the preparation process of N-(triphenylmethyl)-5-(4'-bromomethylbiphenyl-2-yl)tetrazolium (BBTT) crude product

[0036] In a 500...

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Abstract

The invention relates to a green synthesis method of a bromomethylbiphenyl compound, comprising the following steps: dissolving a 4'-methyl-2-substituted biphenyl compound in an organic solvent, adding a bromizating agent to carry out bromination reaction and controlling the reaction conditions to obtain the bromomethylbiphenyl compound. The invention is characterized in that the reaction is carried out in light.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a preparation method of bromomethyl biphenyl compounds. Background technique [0002] Biphenyl occupies an important position in the chemical structural formula of medicines. According to statistics, among the drugs that have been marketed, the drugs containing biphenyl reach 4.6%. ; The molecular size of biphenyl is similar to that of naphthalene ring and benzhydryl, but as a drug structure fragment, it has significant advantages. Studies have shown that due to the suitable flexibility and rigidity of biphenyl, it has a strong binding ability with proteins, which is obviously better than that of benzhydryl and naphthyl. [0003] Bromomethyl biphenyl compounds, especially compounds of structural formula I (4'-bromomethyl-2-substituted biphenyl compounds), are important intermediates for the preparation of sartan antihypertensive drugs, and are the best biphenyl introducing groups...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B39/00C07C255/50C07C253/30C07D257/04
Inventor 刘沫毅李志强邹江杨琰王文峰
Owner CHINA RESOURCES SAIKE PHARMA
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