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Synthetic method of R-1-(4-bromophenyl) ethanol and ester of R-1-(4- bromophenyl) ethanol

A synthesis method and bromophenyl technology are applied in the field of preparation of optically pure chiral alcohols and esters to achieve the effects of overcoming low product yield, good product yield and high application value

Inactive Publication Date: 2015-01-07
王同俊
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the process of splitting and preparing R-1-(4-bromophenyl)ethanol ester, acidic resin is used as racemization catalyst, which not only overcomes the problem of low product yield, but also ensures that the catalyst is cheap, easy to obtain, and repeatable. Utilization, easy to realize industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0009] 1) Preparation of acyl donor p-chlorophenol ester

[0010] Add 500ml of dichloromethane to a 1000ml round bottom flask. Then add 128g (1mol) of p-chlorophenol, 72g (1.2mol) of acetic acid, 247.5g (1.2mol) of DCC, and 2.44g (0.02mol) of DMAP. Stir at room temperature for 10 hours, and detect the disappearance of p-chlorophenol by pointing the plate, then the reaction ends. The solution was filtered, concentrated, and then passed through the column to obtain 156.9 g of pure p-chlorophenol acetate, with a yield of 92.3%.

[0011] Other p-chlorophenol propionate, p-chlorophenol n-butyrate, p-chlorophenol n-valerate etc. can also be prepared according to this example.

[0012] 2) Preparation of R-1-(4-bromophenyl)ethanol ester by dynamic kinetic resolution

[0013] Add 250ml toluene to a 500ml conical flask, then add 100g (0.5mol) 1-(4-bromophenyl)ethanol, 93.5g (1.1mol) p-chlorophenol acetate, 3g CRL, 6g acidic resin CD550. After the addition, the Erlenmeyer flask was s...

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Abstract

The invention relates to a synthetic method of R-1-(4-bromophenyl) ethanol and ester of R-1-(4-bromophenyl) ethanol. The synthetic method comprises the following steps: taking 1-(4-bromophenyl) ethanol as a raw material, lipase as a biological separation catalyst and acidic resin as a racemic catalyst, carrying out dynamic kinetic resolution on chlorophenol ester as an acyl donor to obtain R-1-(4-bromophenyl) ethanol ester and hydrolyzing with LiOH to obtain the R-1-(4- bromophenyl) ethanol. The synthetic method has the advantages of mild conditions, environmental friendliness, good product yield, high selectivity and easiness in obtaining of the used racemic catalyst, thereby having high application value in the industrial production.

Description

technical field [0001] The invention relates to a method for preparing optically pure chiral alcohols and esters, in particular to a method for preparing dynamic kinetic resolution of R-1-(4-bromophenyl)ethanol and esters thereof. Background technique [0002] Chiral drugs are of great significance in the prevention and treatment of many diseases. Since the "reactantrin incident" in the pharmaceutical industry, the research on the synthesis of chiral drugs in human medicine, pesticides, and veterinary drugs has been paid more and more attention by governments and enterprises. Chiral alcohols and chiral esters are one of the important classes of chiral compounds, which can be used as important chiral intermediates and raw materials in the synthesis of pharmaceuticals and fine chemicals. [0003] The currently reported R-1-(4-bromophenyl)ethanol and its esters are mainly obtained by biological resolution of racemic alcohols, which can be further divided into kinetic resolution...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/92C07C33/46C12P41/00C12P7/22
CPCC07C67/08C07B2200/07C07C29/095C12P7/62C12P41/004
Inventor 王同俊
Owner 王同俊
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