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Method for synthesizing 5-isoindolone chloride

The technology of a chloroisoindolinone and a synthetic method is applied in the synthesis field of 5-chloroisoindolinone, can solve the problems such as inability to produce a target compound, a single monobrominated product, no yield, etc., and achieves considerable economic benefits, Easy to scale up production, improve yield effect

Inactive Publication Date: 2013-04-24
CHEMFUTURE PHARMATECH JIANGSU
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The monobromination yield of 4-methoxy-2-methylbenzoic acid methyl ester reported in this patent is very high (98%). For the bromination of 4-chloro-2-methylbenzoic acid methyl ester, using The same method was used, but no specific yield was reported
[0009] Combining the methods of the above literature and the characteristics of the compound itself, we have carried out specific experiments, and the results prove that none of the methods of the above literature can obtain a single monobrominated product, so it is not completely suitable for the production of our target compound

Method used

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  • Method for synthesizing 5-isoindolone chloride
  • Method for synthesizing 5-isoindolone chloride
  • Method for synthesizing 5-isoindolone chloride

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Embodiment 1

[0047] A kind of synthetic method of 5-chloroisoindolinone, concrete steps are as follows:

[0048] Step 1: Esterification to obtain methyl 4-chloro-2-methylbenzoate

[0049]15.4 g of 4-chloro-2-methylbenzoic acid, 1.0 ml of sulfuric acid and 200 ml of methanol were heated to reflux overnight. After distilling off the solvent, dilute with 200 ml of ethyl acetate, wash with 1 M, 100 ml of sodium hydroxide solution, dry over anhydrous sodium sulfate and concentrate to obtain 15.5 g of a colorless oily product with a yield of 93%.

[0050] Step 2: Dibromination reaction to give methyl 4-chloro-2-dibromomethylbenzoate

[0051] 15.5 g of 4-chloro-2-dibromomethylbenzoic acid methyl ester obtained in step 1, 30.0 g of NBS, 2.0 g of benzoyl peroxide and 150 ml of carbon tetrachloride were heated to reflux for 6 hours, and the insoluble solids were removed by filtration. The filtrate was washed with saturated sodium carbonate solution, dried with anhydrous sodium sulfate, concentrate...

Embodiment 2

[0057] A kind of synthetic method of 5-chloroisoindolinone, concrete steps are as follows:

[0058] Step 1: Esterification to obtain methyl 4-chloro-2-methylbenzoate

[0059] 15.0 g of 4-chloro-2-methylbenzoic acid, 1.0 ml of sulfuric acid and 180 ml of methanol were heated to reflux overnight. After distilling off the solvent, dilute with 200 ml of ethyl acetate, wash with 1 M, 100 ml of sodium hydroxide solution, dry over anhydrous sodium sulfate and concentrate to obtain 15.1 g of a colorless oily product with a yield of 93%.

[0060] Step 2: Dibromination reaction to give methyl 4-chloro-2-dibromomethylbenzoate

[0061] 15.1 g of 4-chloro-2-dibromomethylbenzoic acid methyl ester obtained in step 1, 29.2 g of NBS, 2.0 g of benzoyl peroxide and 150 ml of carbon tetrachloride were heated to reflux for 6 hours, and the insoluble solids were removed by filtration. The filtrate was washed with saturated sodium carbonate solution, dried with anhydrous sodium sulfate, concentrat...

Embodiment 3

[0067] A kind of synthetic method of 5-chloroisoindolinone, concrete steps are as follows:

[0068] Step 1: Esterification to obtain methyl 4-chloro-2-methylbenzoate

[0069] 30.0 g of 4-chloro-2-methylbenzoic acid, 2.0 ml of sulfuric acid and 300 ml of methanol were heated to reflux overnight. After distilling off the solvent, dilute with 300 ml of ethyl acetate, wash with 1 M, 100 ml*2 sodium hydroxide solution, dry over anhydrous sodium sulfate and concentrate to obtain 31.0 g of a colorless oily product with a yield of 93%.

[0070] Step 2: Dibromination reaction to give methyl 4-chloro-2-dibromomethylbenzoate

[0071] 31g of 4-chloro-2-dibromomethylbenzoic acid methyl ester, 60.0g NBS, 4.0g benzoyl peroxide and 300ml carbon tetrachloride obtained in step 1 were heated to reflux for 6 hours, filtered to remove insoluble solids, and the filtrate After washing with saturated sodium carbonate solution, it was dried with anhydrous sodium sulfate, concentrated and recrystalli...

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Abstract

The invention discloses a method for synthesizing 5-isoindolone chloride, comprising the following steps: using 4-chlor-2-methyl benzoic acid as an initial reactant; obtaining products through methylation, NBS (N-bromosuccinimide) bromination reaction and amidation reaction in sequence; and obtaining a monobromo pure product through firstly double bromination and then debromination in the NBS bromination reaction. According to the method for synthesizing, the doping of double brominated products when NBS is excessive in the prior art is overcome, and processing is ensured after raw materials are completely reacted without detecting and tracking reaction under the condition that NBS is excessive, so that the cost is reduced, the reaction is easy to control, the complexity of operation is reduced, the purification is relatively simple, and the 5-isoindolone chloride is easy to produce in large scale.

Description

technical field [0001] The invention relates to a synthesis method of 5-chloroisoindolinone, which belongs to the field of organic synthesis. Background technique [0002] At present, the synthesis method of methyl 4-chloro-2-bromomethylbenzoate is in the leading technology: US Patent (US2005 / 143348 A1, 2005 Page column 45; 49; 55), US Patent (US2005 / 239838 A1, 2005 Page column 41), European Patent (WO2005 / 54176 A1, 2005 Page column 136). [0003] The above three patents respectively report the synthesis method of 4-chloro-2-bromomethylbenzoic acid methyl ester, the yield is about 45%, and its synthetic route is: [0004] [0005] However, it has been proved by experiments that dibromine by-products are easy to be generated during the bromination of the above method, and the raw materials are difficult to completely react. If the consumption of NBS is increased, the dibromine products will increase. It is reported in the literature that the product of monobromine is dir...

Claims

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Application Information

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IPC IPC(8): C07D209/46
Inventor 赖文王新俊
Owner CHEMFUTURE PHARMATECH JIANGSU
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