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Preparation method of 3-phenoxybromopropane or analogue thereof

A technology of phenoxybromopropane and analogues, which is applied in the field of drug synthesis, can solve the problems of difficult reaction and complex process operation, and achieve the effects of good catalytic effect, simple process operation and easy control of conditions

Pending Publication Date: 2021-11-23
CHANGSHU INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because hydrogen bromide is gaseous, it is very difficult to realize this reaction, and the actual process operation is more complicated, so it is necessary to find a suitable process to realize this process route easily.

Method used

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  • Preparation method of 3-phenoxybromopropane or analogue thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Preparation of propenyl phenyl ether

[0023] Put 200mL of acetone into the reaction kettle, start stirring, add 18.8g of phenol, 41.5g of potassium carbonate and 26.6g of 3-bromopropene in sequence, raise the temperature to 60°C and keep it warm for 8h, after the reaction is completed, cool down to room temperature, and filter to remove insoluble matter After concentrating the filtrate, ethyl acetate was added, then washed with aqueous sodium carbonate solution, washed with water until neutral, dried and concentrated under reduced pressure to obtain 24.1 g of propenyl phenyl ether, with a yield of 90%. 1 H NMR (400M Hz, CDCl 3 )δ7.38-7.28(m,2H),7.00-6.91(m,3H),6.09(dd,J=17.5,10.5Hz,1H),5.44(d,J=17.5Hz,1H),5.31(d ,J=10.5Hz, 1H), 4.55(d,J=5.5Hz, 2H); 13 C NMR (100M Hz, CDCl 3 ) δ 158.7, 133.5, 129.6, 120.9, 117.7, 114.8, 68.8.

Embodiment 2

[0025] Preparation of propenyl phenyl ether

[0026] Put 200mL of N,N-dimethylformamide into the reaction kettle, start stirring, add 18.8g of phenol, 16g of sodium hydroxide and 22.8g of allylamine in sequence, raise the temperature to 100°C and keep it for 8 hours, and cool down to room temperature after the reaction is completed , filtered to remove insoluble matter, concentrated the filtrate and added dichloromethane, then washed with potassium carbonate aqueous solution and water until neutral, dried and concentrated under reduced pressure to obtain 20.9 g of propenyl phenyl ether, with a yield of 78%. 1 H NMR (400M Hz, CDCl 3 )δ7.38-7.28(m,2H),7.00-6.91(m,3H),6.09(dd,J=17.5,10.5Hz,1H),5.44(d,J=17.5Hz,1H),5.31(d ,J=10.5Hz,1H),4.55(d,J=5.5Hz,2H); 13 C NMR (100M Hz, CDCl 3 ) δ 158.7, 133.5, 129.6, 120.9, 117.7, 114.8, 68.8.

Embodiment 3

[0028] Preparation of propenyl phenyl ether

[0029] Put 200mL of dimethyl sulfoxide into the reaction kettle, start stirring, add 18.8g of phenol, 22.4g of potassium hydroxide and 23.2g of allyl alcohol in sequence, raise the temperature to 100°C and keep it for 8 hours. After the reaction is completed, cool down to room temperature and filter Remove insoluble matter, concentrate the filtrate and add chloroform, then wash with aqueous sodium hydroxide solution and water until neutral, dry and concentrate under reduced pressure to obtain 22.0 g of propenyl phenyl ether with a yield of 82%. 1 H NMR (400M Hz, CDCl 3)δ7.38-7.28(m,2H),7.00-6.91(m,3H), 6.09(dd,J=17.5,10.5Hz,1H),5.44(d,J=17.5Hz,1H),5.31(d ,J=10.5Hz,1H),4.55(d,J=5.5Hz,2H); 13 C NMR (100M Hz, CDCl 3 ) δ 158.7, 133.5, 129.6, 120.9, 117.7, 114.8, 68.8.

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Abstract

The invention discloses a preparation method of 3-phenoxybromopropane or an analogue thereof, which comprises the following steps: carrying out substitution reaction and addition reaction on cheap and easily available phenol or aromatic phenol and an allyl compound thereof to obtain 3-phenoxybromopropane and the analogue thereof, and in order to avoid inconvenience caused by using gaseous hydrogen bromide, the high-concentration hydrobromic acid is generated in situ by adopting the bromide and the acid to realize the second-step addition reaction, the process operation is simple, the conditions are easy to control, the atom economy is good, and the method conforms to the current green chemical synthesis direction in a low-pollution and zero-emission manner from the aspect of environmental influence; and in the aspect of cost economy, the cost is reduced to a great extent due to direct utilization of olefin.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of 3-phenoxybromopropane or its analogues. Background technique [0002] As a commonly used pharmaceutical intermediate, 3-phenoxybromopropane and its analogues are also widely used in the research and development of antitumor and antibacterial drugs. Taking 3-phenoxybromopropane as an example, there are two main synthesis methods at present. Method 1 is to obtain a crude product through direct nucleophilic substitution reaction between phenol and 1,3-dibromopropane, and the crude product is purified by vacuum distillation. This method has low conversion rate, poor selectivity, many by-products, and low purity of the crude product, which must be purified by high-temperature vacuum distillation. and difficult to separate completely. Method 2 is to prepare the product through nucleophilic substitution and bromination reaction of phenol...

Claims

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Application Information

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IPC IPC(8): C07C41/22C07C43/225C07D317/64
CPCC07C41/22C07C41/16C07D317/64C07B39/00C07B41/04C07C43/225C07C43/215
Inventor 杨洋付任重卜文卉曹宝鑫曾小君
Owner CHANGSHU INSTITUTE OF TECHNOLOGY