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Preparation method of 2-(4-bromophenylacetone)-1,3-benzoxazole

A technology of benzoxazole and bromophenyl, which is applied in the field of preparation of 2--1,3-benzoxazole, can solve the problems of harsh reaction conditions, high cost of raw materials, high production difficulty, etc., and achieve high total yield , low cost, environmentally friendly effect

Inactive Publication Date: 2019-09-27
ASTATECH CHENGDU BIOPHARM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this method has fewer process steps, the cost of raw materials is high and expensive catalysts are used, the reaction conditions are harsh, the production is difficult, and it is not easy to synthesize

Method used

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  • Preparation method of 2-(4-bromophenylacetone)-1,3-benzoxazole
  • Preparation method of 2-(4-bromophenylacetone)-1,3-benzoxazole
  • Preparation method of 2-(4-bromophenylacetone)-1,3-benzoxazole

Examples

Experimental program
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Effect test

Embodiment 1

[0029] A kind of preparation method of 2-(4-bromophenyl)-1,3-benzoxazole, the steps are:

[0030] S1. Bromobenzoic acid (50g, 1.0eq) dissolved in toluene (500g) is used as a substrate, and when the substrate is 20°C, thionyl chloride (38.5g, 1.3eq) is slowly dropped into it, and the dropwise addition is completed. The temperature of the system was raised to 40° C. for 1.5 h. After the reaction was complete, it was concentrated to obtain crude p-bromobenzoyl chloride, yield: 100%.

[0031] S2. Under an inert atmosphere, drop p-bromobenzoyl chloride (50g, 1.0eq) dissolved in tetrahydrofuran (500g) into tetrahydrofuran (500g) dissolved in o-aminophenol (49.8g, 2.0eq), at room temperature Reacted for 9h, followed by quenching, adding methyl tert-butyl ether (500g) to the system to extract the organic phase, the organic phase was concentrated to dryness, and column chromatography (PE:MTBE=20:1) gave 4-bromo-N-( 2-Hydroxyphenyl) benzamide, yield: 90%.

[0032] S3. Under inert atmo...

Embodiment 2

[0034] A kind of preparation method of 2-(4-bromophenyl)-1,3-benzoxazole, the steps are:

[0035] S1. Bromobenzoic acid (50g, 1.0eq) dissolved in tetrahydrofuran (250g) is used as a substrate, and when the substrate is 10°C, thionyl chloride (38.5g, 1.3eq) is slowly dropped into it, and the dropwise addition is completed. The temperature of the system was raised to 30° C. to react for 1 h. After the reaction was completed, the product was concentrated to obtain crude p-bromobenzoyl chloride with a yield of 98%.

[0036] S2. Under an inert atmosphere, p-bromobenzoyl chloride (50g, 1.0eq) dissolved in toluene (250g) was dropped into tetrahydrofuran (500g) dissolved in o-aminophenol (49.8g, 2.0eq), at room temperature Reacted for 8h, followed by quenching, adding methyl tert-butyl ether (500g) to the system to extract the organic phase, the organic phase was concentrated to dryness, and column chromatography (PE:MTBE=20:1) gave 4-bromo-N-( 2-Hydroxyphenyl) benzamide, yield: 85%....

Embodiment 3

[0039] A kind of preparation method of 2-(4-bromophenyl)-1,3-benzoxazole, the steps are:

[0040] S1. Bromobenzoic acid (50g, 1.0eq) dissolved in methyl tert-butyl ether (400g) is used as a substrate, and thionyl chloride (38.5g, 1.3eq) is slowly dropped into it when the substrate is 20°C , the dropwise addition was completed, and the system was heated to 40° C. for 1.5 h. After the reaction was completed, it was concentrated to obtain crude p-bromobenzoyl chloride, yield: 95%.

[0041] S2. Under an inert atmosphere, p-bromobenzoyl chloride (50g, 1.0eq) dissolved in methyl tert-butyl ether (400g) was dropped into tetrahydrofuran (500g) dissolved in o-aminophenol (49.8g, 2.0eq) , reacted at room temperature for 9h, then quenched, added methyl tert-butyl ether (500g) to the system to extract the organic phase, concentrated the organic phase to dryness, column chromatography (PE:MTBE=20:1) gave 4- Bromo-N-(2-hydroxyphenyl)benzamide, yield: 88%.

[0042]S3. Under inert atmospher...

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Abstract

The invention discloses a preparation method of 2-(4-bromophenylacetone)-1,3-benzoxazole, and belongs to the field of organic synthesis. According to the preparation method of the 2-(4-bromophenylacetone)-1,3-benzoxazole, the synthesis path is shown in the specification. According to the preparation method of the 2-(4-bromophenylacetone)-1,3-benzoxazole, adopted raw materials are cheap and easy to obtain, the cost is low, the technologic operation is convenient, no ultrahigh temperature special equipment needs to be adopted, safety is high, the total yield is high, and the method is environmentally friendly.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of 2-(4-bromophenyl)-1,3-benzoxazole. Background technique [0002] In 2008, Viirre, Russell, etc. used p-bromobenzaldehyde as a starting material to obtain the target product through a 1-step reaction using the route shown in Figure (1) (referring to Journal ofOrganic Chemistry (2008), 73 (9), 3452 -3459). Although this method has fewer process steps, the two starting materials are not easy to synthesize and are expensive; the reaction uses o-phenanthroline as a solvent, and precious substances such as cesium carbonate and cuprous iodide as raw materials, which are difficult to produce in the production process , Production of large amount of sewage, easy to cause environmental pollution. The reaction formula is as follows: [0003] [0004] In 2012, Tariq, Sana, etc. used p-bromobenzaldehyde as a starting material, and adopted a route as s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/57
CPCC07D263/57
Inventor 李显军庄明晨罗建业郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP