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Process for preparing 4'-halogenalkyl-biphenyl-2-carboxylic acids

An alkyl and aralkyl technology, applied in the fields of chemicals for biological control, carboxylate preparation, chemical instruments and methods, etc., can solve the problems of safety, unsuitable cost, low yield, etc.

Inactive Publication Date: 2011-09-21
SALTIGO GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has the disadvantage that a stoichiometric amount of nickel has to be used but only very low yields are obtained
A disadvantage of this method is that only low yields are achieved
[0009] Common to all methods is that they are either unsuitable for safety and cost reasons, or the current products can only be synthesized by syntheses involving multiple steps and only low yields are achieved

Method used

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  • Process for preparing 4'-halogenalkyl-biphenyl-2-carboxylic acids
  • Process for preparing 4'-halogenalkyl-biphenyl-2-carboxylic acids
  • Process for preparing 4'-halogenalkyl-biphenyl-2-carboxylic acids

Examples

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example

[0105] 1. Preparation of monoisopropyl phthalate

[0106]Suspend phthalic anhydride (14.8 g, 100 mmol) in a 100 ml round bottom flask with reflux condenser i PrOH (isopropanol) (50ml) and heated at the boil for 6 hours. After cooling the clear solution to room temperature, it was concentrated by evaporation and the remaining colorless oily residue was dried in vacuo, during which time it slowly crystallized out and the product was obtained as a colorless solid ( 20.8 g, 99%). 1 H-NMR (600MHz, CDCl 3 )δ=12.46(s, 1H), 7.85(d, 3 J=7.6Hz, 1H), 7.64(d, 3 J=7.6Hz, 1H), 7.54(t, 3 J=7.6Hz, 1H), 7.49(t, 3 J=7.6Hz, 1H), 5.24(h, 3 J=6.2Hz, 1H), 1.32(d, 3 J = 6.7 Hz, 6H) ppm. 13 C-NMR (151MHz, CDCl 3 ) δ = 172.6, 167.5, 133.7, 132.0, 130.4, 129.6, 129.5, 128.5, 69.5, 21.3 ppm.

[0107] 2. Preparation of Potassium Monoisopropyl Phthalate

[0108] Monoisopropyl phthalate (10.4 g, 50.0 mmol) was dissolved in 2-propanol (20 ml) in a 250 ml round bottom flask. A solution of potass...

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Abstract

The invention relates to a process for preparing a 4'-halogenalkyl-biphenyl-2-carboxylic acid. The invention relates to a process for preparing the optionally substituted 4'-halogenalkyl-biphenyl-2-carboxylic ester and to a process for preparing the corresponding optionally substituted 4'-halogenalkyl-biphenyl-2-carboxylic acid. A process for preparing a compound with the following chemical formula (I), wherein R1 is an alkyl group with C1-C6, an aryl group with C6-C24 or an aralkyl group with C7-C15, and R2 can be independent of each other or same, n=1, 2, 3 or 4; a compound with the following chemical formula (II) is reacted with a compound with the following chemical formula (III) in the presence of at least one copper source, at least one cyclic chelating amine, at least one phosphine ligand and at least one palladium source to generate the compound with the chemical formula (I), wherein cat is an inorganic or organic single-charge cation, and X is a halogen element which is equal to Cl, Br, I, pseudo halogen, aryl sulphonate ester or alkylsulfonic acid ester.

Description

technical field [0001] The present invention relates to a process for the preparation of optionally substituted 4'-haloalkyl-biphenyl-2-carboxylates and to a process for the preparation of the corresponding optionally substituted 4'-haloalkane The method of base biphenyl-2-carboxylic acid. Background technique [0002] 4'-Haloalkylbiphenyl-2-carboxylic acid is an important intermediate used in the manufacture of pharmaceuticals. In particular, 4'-trifluoromethylbiphenyl-2-carboxylic acid itself is a known pharmaceutically active ingredient under the name biferepine. Bifepripine lowers the cholesterol content as well as the triglyceride fraction in the blood plasma (Arteriosclerosis, 1987, 64, 27-35). Therefore 4'-trifluoromethylbiphenyl-2-carboxylic acid is a drug for the treatment of heart and circulatory disorders. 4'-Haloalkylbiphenyl-2-carboxylic acids can be prepared in a manner known per se by saponification of 4'-haloalkylbiphenyl-2-carboxylates. [0003] JP ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C63/72C07C51/09C07C69/76C07C67/343A01P9/00
CPCC07B37/04C07C51/09C07C67/08C07C67/30C07C67/343C07C69/80C07C63/72C07C69/76
Inventor 迈克尔·克雷斯阿兰·科泰安特耶·施泰因豪斯卢卡斯·戈森斯托马斯·克诺贝尔
Owner SALTIGO GMBH
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