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Synthesis method of 4'-Bromomethyl-2-cyanobiphenyl

A technology of bromomethylbiphenyl and synthesis method, applied in the field of synthesis of 2-cyano-4'-bromomethylbiphenyl, achieving the effects of environmental protection, low cost and high yield

Active Publication Date: 2009-12-09
ASYMCHEM LIFE SCI TIANJIN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

By reacting with inexpensive bromine as a brominating agent, but producing an equivalent amount of hydrogen bromide as a by-product
Because the by-product hydrogen bromide inhibits the reaction, it is necessary to supplement the free radical initiator to complete the reaction. In addition, the defect of the method is the same as method 2), and the product needs to be further purified

Method used

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  • Synthesis method of 4'-Bromomethyl-2-cyanobiphenyl
  • Synthesis method of 4'-Bromomethyl-2-cyanobiphenyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: Preparation of 2-cyano-4'-bromomethylbiphenyl, the steps are as follows:

[0029] 1) Add 771g of dichloromethane (10mL / g), 58g of 4'-methyl-2-cyanobiphenyl (1.0eq), 0.5g of 2,2'-azobisisobutyronitrile to a 2L reaction flask in sequence (0.01eq) and 80.1g bromosuccinimide (1.5eq), the bromination reaction was carried out for 4h at a temperature of 45-55°C and a flow rate of 5L / s nitrogen;

[0030] 2) After the reaction solution was lowered to normal temperature, press-filtered, then added 49.7g of diethyl phosphite (1.2eq) to the filtrate, and reacted at 25-35°C for 10h;

[0031] 3) Concentrate the reaction solution under reduced pressure at a temperature of 45-55°C, pump in 405g of pure water (7mL / g) for crystallization once, and obtain 2-cyano-4'-methyl bromide after separation The base biphenyl product was 70.3g, the yield was 86%, and the detection showed that the liquid chromatography purity (HPLC) was 98%. The hydrogen nuclear magnetic spectrum data...

Embodiment 2

[0032] Embodiment 2: Preparation of 2-cyano-4'-bromomethylbiphenyl, the steps are as follows:

[0033] 1) Add 617g of dichloromethane (12mL / g), 39g of 4'-methyl-2-cyanobiphenyl (1.0eq), and 3.3g of 2,2'-azobisisobutyronitrile in sequence in a 2L reaction flask (0.1eq) and 35.6g bromosuccinimide (1.0eq), the bromination reaction was carried out for 5h at a temperature of 45-55°C and a flow rate of 10L / s nitrogen;

[0034] 2) After the reaction solution was lowered to normal temperature, press filter, then add 27.6g of diethyl phosphite (1.0eq) to the filtrate, and react at 25-35°C for 14h;

[0035] 3) Concentrate the reaction solution under reduced pressure at a temperature of 45-55°C, pump in 464g of pure water (12mL / g) for crystallization once, and obtain 2-cyano-4'-methyl bromide after separation Base biphenyl product 43g, yield 82%, detection shows that liquid chromatography purity (HPLC) is 98%. The hydrogen nuclear magnetic spectrum data (1H-NMR) is: (300MHZ, CDCl3), δ4...

Embodiment 3

[0036] Embodiment 3: Preparation of 2-cyano-4'-bromomethylbiphenyl, the steps are as follows:

[0037] 1) Add 925g of dichloromethane (18mL / g), 39g of 4'-methyl-2-cyanobiphenyl (1.0eq), 6.5g of 2,2'-azobisisobutyronitrile in sequence in a 2L reaction flask (0.2eq) and 78g bromosuccinimide (2.2eq), carry out the bromination reaction for 4.5h at a temperature of 45-55°C and a flow rate of 8L / s nitrogen gas

[0038] 2) After the reaction solution was lowered to normal temperature, press filter, then add 69g of diethyl phosphite (2.5eq) to the filtrate, and react at 25-35°C for 11h;

[0039]3) Concentrate the reaction solution under reduced pressure at a temperature of 45-55°C, pump in 695g of pure water (18mL / g) for crystallization once, and obtain 2-cyano-4'-methyl bromide after separation Base biphenyl product 40g, yield 81%, detection shows that liquid chromatography purity (HPLC) is 98%. The hydrogen nuclear magnetic spectrum data (1H-NMR) is: (300MHZ, CDCl3), δ4.56 (methyl...

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Abstract

The invention relates to a synthesis method of 4'-Bromomethyl-2-cyanobiphenyl, comprising the following preparation steps: 1) adding halogenated hydrocarbon solvent, 4'-Methyl-2-cycanobiphenyl, radical initiator and brominating agent in sequence into a reactor, evenly mixing them, and carrying out bromination reaction with the introduced nitrogen at the temperature of about 5 DEG C; 2) filter-pressing the reaction liquid after the reaction liquid is lowered to normal temperature, and then adding diethyl phosphite into the filter liquid to fully react at the temperature of about 30 DEG C; 3) performing reduced pressure concentration on the reaction product at the temperature of about 50 DEG C, and pumping pure water in for crystallization, to obtain the product of the invention after separation. The invention has the advantages of abundant raw material, low cost and high yield, and can directly obtain monobromo aromatic ring without separation and purification; the invention is finished by controlling lead-in speed of nitrogen under the condition of supplementing no radical initiator and can effectively discharge the rest bromine in time; the invention has stable process condition and simple operation, reduces three-waste discharge, and is suitable for industrial scale production.

Description

(1) Technical field [0001] The invention relates to a synthesis method of 2-cyano-4’-bromomethylbiphenyl. (2) Background technology [0002] Hypertension is a major risk factor for cardiovascular, cerebral and renal vascular diseases. If left untreated, it can lead to serious consequences. Although there are currently many types of antihypertensive drugs, a considerable number of patients with hypertension fail to obtain effective blood pressure treatments. control. The ideal antihypertensive drug should not only be effective but also have low side effects. The emergence of angiotensin II (Ang II) receptor (AT1) antagonists represents an important development in the treatment of hypertension, making antagonizing the circulating and local Ang II effects at the receptor level a new concept in current antihypertensive drug treatment and new method. [0003] Sartan drugs are first-line antihypertensive drugs. They have a new antihypertensive mechanism, stable blood pressure r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/50C07C253/30
Inventor 洪浩陈迥张席妮黄鲁宁
Owner ASYMCHEM LIFE SCI TIANJIN
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