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A kind of preparation method of o-fluorobenzaldehyde

A technology of fluorobenzaldehyde and benzaldehyde, which is applied in the field of preparation of o-fluorobenzaldehyde, can solve the problems of large consumption of catalyst, environmental pollution, reduction of the scope of use of o-fluorobenzaldehyde and the like

Active Publication Date: 2022-02-01
SINOPHARM CHEM REAGENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The above methods have the following problems: firstly, large-scale chlorination reduces the scope of use of o-fluorobenzaldehyde, and some high-end industries cannot use it; secondly, large-scale hydrolysis needs to consume a large amount of catalyst and produce a large amount of waste acid , waste water, causing serious pollution to the environment; finally, the cumbersome process steps greatly increase the production cost; the highly toxic chlorine gas strictly controlled by the state is used, and the diazotization reaction and photochlorination reaction restricted by the state are adopted

Method used

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  • A kind of preparation method of o-fluorobenzaldehyde

Examples

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Embodiment 1

[0034] A preparation method of o-fluorobenzaldehyde, comprising the following steps:

[0035] (1) 1.25 moles of propyl formate were dissolved in 150 ml of anhydrous tetrahydrofuran to obtain solution A.

[0036] (2) 1 mole of o-fluorobromobenzene was dissolved in 200 ml of anhydrous tetrahydrofuran to obtain solution B.

[0037] (3) Put 1 mole of anhydrous lithium chloride and 1.15 moles of magnesium into a reaction flask, add 50 ml of anhydrous tetrahydrofuran, heat to a slight boil (about 65 ° C), and drop 2 ml of dibromoethane to initiate the reaction.

[0038] (4) Under reflux, solution B was added dropwise into the above-mentioned reaction flask, and the temperature was controlled at 63-67°C during the process.

[0039] (5) After feeding, cool down to 20-30°C, add solution 1 dropwise; react for 1 hour after feeding.

[0040] (6) Cool down to below 10°C, quench with dilute hydrochloric acid, post-process, and refine by vacuum distillation.

[0041] (7) 113.5 g of o-fluo...

Embodiment 2

[0043] A preparation method of o-fluorobenzaldehyde, comprising the following steps:

[0044] (1) 1 mole of propyl formate was dissolved in 100 ml of anhydrous tetrahydrofuran to obtain solution A.

[0045] (2) 1 mole of o-fluorobromobenzene was dissolved in 150 ml of anhydrous tetrahydrofuran to obtain solution B.

[0046] (3) Put 1 mole of anhydrous lithium chloride and 1.15 moles of magnesium into a reaction flask, add 30 ml of anhydrous tetrahydrofuran, heat to a slight boil (about 65° C.), and drop 2 ml of dibromoethane to initiate the reaction.

[0047] (4) Under reflux, solution B was added dropwise into the above-mentioned reaction flask, and the temperature was controlled at 63-67°C during the process.

[0048] (5) After feeding, cool down to 20-30°C, add solution 1 dropwise; react for 0.5 hours after feeding.

[0049] (6) Cool down to below 10°C, quench with dilute hydrochloric acid, post-process, and refine by vacuum distillation.

[0050] (7) 110 g of o-fluorobe...

Embodiment 3

[0052] A preparation method of o-fluorobenzaldehyde, comprising the following steps:

[0053] (1) 1.5 moles of propyl formate were dissolved in 200 ml of anhydrous tetrahydrofuran to obtain solution A.

[0054] (2) 1 mole of o-fluorobromobenzene was dissolved in 250 ml of anhydrous tetrahydrofuran to obtain solution B.

[0055] (3) Put 1 mole of anhydrous lithium chloride and 1.15 moles of magnesium into a reaction flask, add 70 ml of anhydrous tetrahydrofuran, heat to a slight boil (about 65° C.), and drop 2 ml of dibromoethane to initiate the reaction.

[0056] (4) Under reflux, solution B was added dropwise into the above-mentioned reaction flask, and the temperature was controlled at 63-67°C during the process.

[0057] (5) After feeding, cool down to 20-30°C, add solution 1 dropwise; react for 1.5 hours after feeding.

[0058] (6) Cool down to below 10°C, quench with dilute hydrochloric acid, post-process, and refine by vacuum distillation.

[0059] (7) 115 g of o-fluo...

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Abstract

The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a preparation method of o-fluorobenzaldehyde, comprising the following steps: dissolving propyl formate in anhydrous tetrahydrofuran to obtain solution A; dissolving o-fluorobromobenzene in anhydrous tetrahydrofuran , to obtain solution B; put anhydrous lithium chloride and magnesium into the reaction flask, add anhydrous tetrahydrofuran, heat to slightly boil, drop dibromoethane to initiate the reaction; under reflux, add solution B to the reaction flask; feeding is complete , lower the temperature, and then add solution A dropwise; after feeding, continue the reaction for a period of time; lower the temperature, quench with dilute hydrochloric acid, post-process, and refine by vacuum distillation to obtain o-fluorobenzaldehyde. The method of the present invention forms stable and less active benzylmagnesium lithium chloride by adding lithium chloride when preparing the Grignard reagent; the reaction of propyl formate with it is controllable, and only reacts with a less active benzylmagnesium lithium chloride, so that The reaction stays at the aldehyde stage instead of going further to the alcohol stage.

Description

technical field [0001] The invention relates to the field of synthesis of pharmaceutical intermediates, in particular to a preparation method of o-fluorobenzaldehyde. Background technique [0002] O-Fluorobenzaldehyde is an important intermediate in organic synthesis, which is widely used in medicine, dyestuff, pesticide and so on. In medicine, it can be used in the synthesis of various drugs such as antihypertensive drugs, antipyretic, analgesic and anti-inflammatory drugs, anticancer drugs, and muscle relaxants. In the synthesis of dyes, the new dyes synthesized with it as raw materials have excellent properties such as luster, light fastness, water resistance and organic solvents; in the production of pesticides, the pesticides synthesized with it as raw materials have higher biological activity, It has the characteristics of long-lasting drug effect and small side effects. [0003] The current industrial synthesis of o-fluorobenzaldehyde has the following methods: [...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/55C07C45/00
CPCC07C45/00C07C47/55
Inventor 郭建国凌芳秦建国宋忠哲
Owner SINOPHARM CHEM REAGENT
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