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Method for preparing p-fluorobenzaldehyde

A technology of p-fluorobenzaldehyde and p-fluorobenzoic acid, which is applied in the field of preparation of pharmaceutical intermediate p-fluorobenzaldehyde, can solve the problems of separation of ortho isomers, high toxicity of solvents, etc., and achieve few synthesis steps, single product, Avoid the effects of catalyst use

Inactive Publication Date: 2011-05-04
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent CN101353297A mentions that the method for preparing p-fluorobenzaldehyde is to synthesize p-chlorobenzaldehyde and potassium fluoride under catalyst and high temperature conditions. The raw material price of this method is cheap, the synthesis route is short, and the discharge of three wastes is less. The disadvantage is that the catalyst is used and the reaction is carried out under high temperature conditions, and the solvent used is relatively toxic
This synthesis method has high purity and yield, but the disadvantage is that the dichloromethyl ether method in the fluorobenzoylation method needs to separate the ortho isomers, etc.

Method used

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  • Method for preparing p-fluorobenzaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0029] (1) Preparation of N-methyl-N-methoxy p-fluorobenzamide

[0030] Under nitrogen protection, add toluene (15mL), p-fluorobenzoic acid (6.05g, 0.043mol), phosphoramidite P(NMeOMe) in sequence in a 100mL two-necked flask 3 (3.76g, 0.018mol), the mixture was reacted at 60°C for 30 minutes. After the completion of the reaction detected by TLC, the reaction was quenched with saturated sodium bicarbonate solution (100mL); extracted with ether (15mL×3), the organic phase was washed with water (10mL×2) and saturated brine (20mL) successively, and dried over anhydrous sodium sulfate ; The solvent was evaporated under reduced pressure and separated by column chromatography (petroleum ether / ethyl acetate=4:1) to obtain a colorless liquid (4.72g), which was N-methyl-N-methoxy-p-fluorobenzamide. The yield is 90%.

[0031] The N-methyl-N-methoxy p-fluorobenzamide of above-mentioned synthesis, through 1 HNMR, 13 CNMR, IR detection, the product is a pure target compound. Its variou...

Embodiment 2

[0038] (1) Preparation of N-methyl-N-methoxy p-fluorobenzamide

[0039] Add p-fluorobenzoic acid (6.05g, 0.043mol) and PhP 3 (11.27g, 0.043mol), then THF (15mL) was added, the mixture was cooled to about 0°C, NBS (8.42g, 0.047mol) was added in batches under stirring, and stirred for 30 minutes. Continue to add NH(OMe)Me (4.46g, 0.073mol) to the above reaction solution, after the completion of the reaction was detected by TLC, the reaction was quenched with saturated sodium bicarbonate solution (100mL); ether extraction (15mL×3), organic phase Wash with water (10mL×2) and saturated brine (20mL) once, and dry over anhydrous sodium sulfate; evaporate the solvent under reduced pressure, and separate by column chromatography (petroleum ether / ethyl acetate=4:1) to obtain a colorless liquid (4.52 g), which is N-methyl-N-methoxy-p-fluorobenzamide. The yield was 86%.

[0040] (2) Preparation of p-fluorobenzaldehyde

[0041] Same as Example 1.

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Abstract

The invention discloses a method for preparing p-fluorobenzaldehyde, and belongs to the technical field of chemical analysis. N-methyl-N-methoxyl p-fluorobenzamide is synthesized by parafluorobenzoic acid serving as a raw material under the action of an amidation reagent and reduced by vitride solution to directly obtain the p-fluorobenzaldehyde, so that synthesis steps are a few, the method is easy to operate, the product is single, and the yield is high (the total yield of 59.4 percent); the vitride solution serving as a reducing agent has higher reducibility, stable property and lower price, and is convenient to store; the parafluorobenzoic acid serving as the raw material is easy to purchase and has low cost, so that good conditions are created for the mass industrial production and commercialization of the product; and the adopted raw material is nontoxic, and a catalyst is not used in the production process, so that the method is environmental-friendly, and low in emission and accords with the national industrial policy.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a preparation method of a pharmaceutical intermediate p-fluorobenzaldehyde. Background technique [0002] 4-Fluorobenzaldehyde (PFDA for short) is a very important organic synthesis intermediate, which can be used in the synthesis of fine chemical products such as medicine, pesticide, dye and surfactant, and can also be used as cosmetics and plastic additives, plant protection agents, and bactericides. Synthesis of agents, deodorants, etc. For example, in medicine, it can be used to synthesize the drugs haloperol and droperidol for the treatment of nervous system diseases, and the blood lipid-lowering drugs rosuvastatin and lipitor. In addition, p-fluorobenzaldehyde can also be used to synthesize antipyretic, analgesic and anti-inflammatory drugs, anticancer drugs and muscle relaxants, etc.; in pesticides, it can be used to synthesize cyfluthrin (centrin), which is a br...

Claims

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Application Information

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IPC IPC(8): C07C47/55C07C45/41
Inventor 胡雨来曹瑞雲黄丹凤
Owner NORTHWEST NORMAL UNIVERSITY
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