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Preparation method of 2-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: 2019-04-16
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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  • Preparation method of 2-fluorobenzaldehyde

Examples

Experimental program
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Effect test

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) Solution B in which 1 mole of o-fluorobromobenzene is dissolved in 200 ml of anhydrous tetrahydrofuran.

[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-fluoro...

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) Solution B in which 1 mole of o-fluorobromobenzene is dissolved in 150 ml of anhydrous tetrahydrofuran.

[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-fluorobenz...

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) Solution B in which 1 mole of o-fluorobromobenzene is dissolved in 250 ml of anhydrous tetrahydrofuran.

[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-fluoro...

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Abstract

The invention relates to the technical field of medical intermediate synthesis, in particular to a preparation method of 2-fluorobenzaldehyde. The method comprises the following steps that propyl formate is dissolved into anhydrous tetrahydrofuran, and a solution A is obtained; 2-bromofluorobenzene is dissolved into anhydrous tetrahydrofuran, and a solution B is obtained; anhydrous lithium chloride and magnesium are put into a reaction flask, anhydrous tetrahydrofuran is added, heating is conducted to micro-boiling, dibromoethane is dropwise added, and a reaction is triggered; under backflow,a solution B is added into the reaction bottle; feeding is finished, cooling is conducted, and the solution A is dropwise added; feeding is finished, and the reaction continues to be conducted for a period of time; cooling is conducted, diluted hydrochloric acid is quenched, aftertreatment is conducted, vacuum distillation refining is conducted, and 1-phenyl-2-butanone is obtained. According to the method, when a Grignard reagent is prepared, astable benzyl magnesium lithium chloride low in activity is formed by adding lithium chloride; a reaction of propyl formate and the benzyl magnesium lithium chloride is controllable, propyl formate only reacts with one benzyl magnesium lithium chloride, and the reaction is stopped at the aldehyde stage but not further goes 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 Applications(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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