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Preparing method of 3,5-halogeno benzene carboxylic acid

A technology of dihalogenated benzene carboxylic acid and halogenated reagent, which is applied in the field of preparation of 3,5-halogenated benzene carboxylic acid, can solve the problems of non-disclosure and the like, and achieve the effects of simple operation, easy industrial production and mild reaction conditions

Inactive Publication Date: 2015-11-25
烟台九目化学股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The preparation method of 3,5-halogenated benzenecarboxylic acid is not disclosed in the literature

Method used

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  • Preparing method of 3,5-halogeno benzene carboxylic acid
  • Preparing method of 3,5-halogeno benzene carboxylic acid
  • Preparing method of 3,5-halogeno benzene carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: 3-chloro-5-bromobenzoic acid

[0020] 3-Chloro-4-aminobenzoic acid ethyl ester

[0021]

[0022] In a 250ml round bottom flask, add ethyl 4-aminobenzoate (10g, 60mmol), 80ml of ethanol with a mass fraction of 95%, under nitrogen protection, stir and heat up to 60°C, add N-chlorosuccinimide ( 8g, 60mmol), stirred for 8 hours, followed the reaction by TLC until the raw material point disappeared, the reaction system evaporated ethanol under reduced pressure, and the residue was boiled to pH=7 with 100ml of water, and 6g of yellow solid was obtained by crystallization, with a yield of 50%. 1 H-NMR (500MHz, CDCl 3 , ppm): 4.20 (2H, NH 2 ), 6.75 (1H, d, ArH), 7.46 (1H, d, ArH), 7.67 (1H, s, ArH), 4.30 (2H, q, CH 2 ), 1.30 (3H, t, CH 3 ), the detection result is ethyl 3-chloro-4-aminobenzoate.

[0023] 3-Chloro-4-amino-5-bromobenzoic acid ethyl ester

[0024]

[0025] In a 250ml round bottom flask, add ethyl 3-chloro-4-aminobenzoate (10g, 50mmol), 80ml ...

Embodiment 2

[0032] Example 2: 3-chloro-5-bromophenylacetic acid

[0033] 3-Chloro-4-aminophenylacetic acid ethyl ester

[0034]

[0035] In a 250ml round bottom flask, add ethyl 4-aminophenylacetate (10g, 55.8mmol), 80ml of isopropanol, under nitrogen protection, stir and heat up to 60°C, add N-chlorosuccinimide (7.4g , 55.8mmol), stirred for 8 hours, followed the reaction by TLC until the raw material point disappeared. The solvent isopropanol was distilled off from the reaction solution under reduced pressure, and the residue was boiled with 100 ml of water until pH = 7. Then, 5.9 g of a yellow solid was obtained by crystallization, with a yield of 50%. 1 H-NMR (500MHz, CDCl 3 , ppm): 7.42 (1H, d, ArH), 7.18 (1H, q, ArH), 6.64 (1H, d, ArH), 4.13 (2H, q, CH 2 ), 4.02 (2H, s, NH 2 ), 3.59 (2H, s, CH 2 ), 1.21 (3H, t, CH 3 ), the detection result is ethyl 3-chloro-4-aminophenylacetate.

[0036] 3-Chloro-4-amino-5-bromophenylacetic acid ethyl ester

[0037]

[0038] In a 250ml...

Embodiment 3

[0045] Embodiment 3: 3-chloro-5 iodobenzoic acid

[0046] 2-Amino-5-chlorobenzoic acid ethyl ester

[0047]

[0048] In a 250ml round bottom flask, add ethyl anthranilate (10g, 60mmol), industrial methanol 80ml, under nitrogen protection, stir and heat up to 60°C, add N-chlorosuccinimide (8g, 60mmol), After stirring for 8 hours, the reaction was tracked by TLC until the raw material point disappeared. Methanol was distilled off from the reaction system under reduced pressure, and the residue was boiled with 100 ml of water until pH = 7. Then, 6 g of a yellow solid was obtained by crystallization, with a yield of 50%. 1 H-NMR (500MHz, CDCl 3 , ppm): 7.49 (1H, d, ArH), 7.11 (1H, q, ArH), 6.62 (1H, d, ArH), 5.63 (2H, s, NH 2 ), 4.29 (2H,q,CH 2 ), 1.30 (3H, t, CH 3 ), the detection result is ethyl 2-amino-5-chlorobenzoate.

[0049] 2-Amino-3-iodo-5-chlorobenzoic acid ethyl ester

[0050]

[0051] In a 250ml round bottom flask, add ethyl 2-amino-5-chlorobenzoate (10g, ...

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Abstract

The invention relates to a preparing method of 3,5-halogeno benzene carboxylic acid, which comprises the steps: taking a compound I or compound II as a raw material, adding a halogenating reagent into the compound I or compound II, then dissolving in an alcohol solvent, under nitrogen protection, controlling temperature at 30-60 DEG C, and generating an intermediate compound III or compound IV through a halogenating reaction; placing the compound III or compound IV into glacial acetic acid, controlling temperature at 0+ / -10 DEG C, adding sodium nitrite to perform diazo-reaction in the glacial acetic acid, then dropwise adding the reaction liquid into a sodium hypophosphite water solution or hypophosphorous acid solution to perform reduction reaction and generate an intermediate compound V; hydrolyzing and acidizing the compound V to generate a target product compound VI. The preparing method is performed at normal pressure, used raw materials are easy to obtain, reaction conditions are mild, operation is simple and yield is high.

Description

technical field [0001] The invention relates to a preparation method of 3,5-halogenated benzenecarboxylic acid, which belongs to the field of chemical synthesis. Background technique [0002] 3,5-Halobenzenecarboxylic acid is mainly used in pharmaceutical intermediates and liquid crystal raw materials. It has a broad market application prospect, and the annual market consumption is huge. The preparation of 3,5-halogenated benzenecarboxylic acids is not disclosed in the literature. Contents of the invention [0003] The technical problem to be solved by this invention is to provide a kind of preparation method of 3,5-halogenated benzene carboxylic acid, this preparation method is carried out under normal pressure, with 4-aminobenzene carboxylate or 2-aminobenzene carboxylate as The starting material is prepared by halogenation reaction, diazotization reaction, reduction reaction and decarboxylation reaction to prepare the general formula 3,5-halogenated benzene carboxylic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C63/70C07C227/16C07C229/60C07C67/317C07C69/76C07C229/56
CPCC07C51/09C07C67/317C07C227/16C07C229/60C07C69/76C07C229/56C07C63/70
Inventor 柳佳欣陈慕欣程大兴李向阳陈倩倩李海艳
Owner 烟台九目化学股份有限公司
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