Preparation method of 4-(3-fluorine benzyloxy) benzaldehyde
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A technology of fluorobenzyloxy and p-hydroxybenzaldehyde, which is applied in the field of preparation of 4-benzaldehyde, can solve problems such as complex processing methods, difficult crystallization, and difficulty in industrialization, and achieve stable process, simple post-processing method, and simplified operation Effect
Inactive Publication Date: 2017-07-25
SHANDONG XINHUA PHARMA CO LTD
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[0006] (3) low yield, only 92.6%
[0007] (4) The post-treatment method is extremely complicated: 1) filter and wash to remove inorganic salts; 2) evaporate the solvent; 3) add water to dissolve, and extract with toluene; 4) evaporate toluene; 5) tol
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Embodiment 1
[0026] Add 28.92g (200mmol) of compound II, 24.42g (200mmol) of compound III, 210mmol of potassium carbonate, and 150ml of acetonitrile, and heat up to reflux for 12h. The solvent was evaporated to obtain an oily product, which was added with 150 ml of water, stirred and cooled to crystallize, filtered at room temperature, and dried to obtain Compound I with a yield of 97.04% and an HPLC content of 99.53%.
[0027] The prepared compounds were tested, and the structural confirmation data are as follows:
[0032] Add 28.92g (200mmol) of compound II, 24.42g (200mmol) of compound III, 240mmol of sodium carbonate, and 290ml of acetonitrile, and heat up to reflux for 12 hours. The solvent was evaporated to obtain an oily product, which was added with 290 ml of water, stirred and cooled to crystallize, filtered at room temperature, and dried to obtain Compound I with a yield of 97.22% and an HPLC content of 99.47%.
Embodiment 3
[0034] Add 28.92g (200mmol) of compound II, 24.42g (200mmol) of compound III, 220mmol of sodium carbonate, and 250ml of acetonitrile, and heat up to reflux for 10h. The solvent was evaporated to obtain an oily substance, which was added with 250ml of water, stirred and cooled to crystallize, filtered at room temperature, and dried to obtain Compound I with a yield of 97.52% and an HPLC content of 99.55%.
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Abstract
The invention belongs to the field of pharmaceutical chemistry, and particularly relates to a preparation method of 4-(3-fluorine benzyloxy) benzaldehyde. The preparation method comprises the following steps: adding fluorobenzyl chloride, p-hydroxy benzaldehyde, an acid-binding agent and acetonitrile into a reaction bottle, and performing heating reflux reaction; after the reaction is completed, boiling off the acetonitrile, and adding water for re-rectification, thus obtaining the 4-(3-fluorine benzyloxy) benzaldehyde. The acid-binding agent is potassium carbonate or sodium carbonate. According to the preparation method, no catalyst is added, so that use of sodium iodide or potassium iodide is avoided, and the cost is low; by the adoption of the inert solvent acetonitrile serving as a solvent, the reaction effect is unexpectedly good, and side reaction is less; water rectification can remove both inorganic salt and organic impurities; a post-treatment method is greatly simplified; the process is stable, easy to operate, high in operability and suitable for industrial production; the yield is 97.0 percent or above, and the HPLC content is up to 99.0 percent or above.
Description
technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of 4-(3-fluorobenzyloxy)benzaldehyde. Background technique [0002] Safinamide was developed by Newron Pharmaceuticals to improve motor and cognitive function in people with Parkinson's disease. [0003] CN105061245A provides a method for preparing high-purity safinamide, and discloses the preparation of 4-(3-fluorobenzyloxy)benzaldehyde, the reaction of m-fluorochlorobenzyl (or m-fluorobromobenzyl) with p-hydroxybenzaldehyde, The reaction solvent is alcohols (methanol, ethanol, isopropanol) or toluene, the catalyst is sodium iodide, the post-treatment method: filter and wash to remove inorganic salts, evaporate the solvent, add water to dissolve and extract with toluene, evaporate toluene, toluene / n-hexane The target product was obtained by recrystallization of alkane with a yield of 92.6%. There are following disadvantages: [0004] (1) It ...
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