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Method for preparing 7-bromine-1-heptylene

A technology of heptene, the main raw material, applied in the field of synthesis of heptene derivatives, which can solve the problems of producing a large amount of waste residue, not suitable for large-scale production, and high reaction temperature

Active Publication Date: 2012-09-19
ASYMCHEM LAB TIANJIN +4
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AI Technical Summary

Problems solved by technology

[0005] 1. High-temperature elimination method: use 1,7-dibromoheptane as the starting material, add hexamethylphosphoric triamide, and react at 258°C to obtain the final product 7-bromo-1-heptene. The method has few steps and is easy to operate, but the suppliers of starting materials are few and expensive, the reaction temperature is high, the reaction conditions are harsh, and the by-product 1,6-heptadiene is produced in the reaction process, and the reaction yield is very low, so it is not suitable for mass production
[0006] 2. Grignard reagent method: use 1,4-dibromobutane as the starting material, add copper lithium reagent, allyl magnesium bromide, and react under nitrogen protection to obtain the final product 7-bromo-1-heptene , this method has few steps, simple operation and high yield, but the raw material allylmagnesium bromide used in the process is difficult to prepare, and the price is expensive, the reaction produces many by-products, the product is difficult to purify, and is not suitable for large-scale production Production
[0007] 3. Grignard reagent method: use 1,4-dibromobutane as the starting material, react with Grignard reagent and bromine to obtain 1,2,7-tribromoheptane, and then in the presence of zinc powder Eliminate, obtain final product 7-bromo-1-heptene through two steps, the price of this method starting material is cheap, and step is simple, and total yield is higher, but aftertreatment rectification condition is harsh, produces a large amount of waste residues in the process, Therefore, it is not suitable for industrial production

Method used

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Experimental program
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Effect test

Embodiment 1

[0031] Embodiment 1: A kind of preparation 7-bromo-1-heptene The method is characterized in that the specific preparation steps are as follows:

[0032] (1) Ring-opening reaction: Add 200kg of main raw materials tetrahydrofuran and 19kg (0.07eq) of concentrated sulfuric acid to a 1000L reactor in sequence, control the temperature of the system at 2±2°C, and slowly add 420kg (0.9eq) of 48% hydrobromic acid aqueous solution dropwise , after dropping, raise the temperature to 80±2°C, keep it warm for 3h, after the reaction is completed, cool down to 0±2°C, adjust the pH of the system to 7-8 with 23kg (0.1eq) of sodium bicarbonate, extract, wash the organic phase, and concentrate to obtain Oily product 4-bromo-1-butanol 286kg, yield 67.5%, gas chromatography purity (GC): 97.0%;

[0033] (2) Hydroxyl protection: Add the main raw material 4-bromo-1-butanol to the 1000L reactor in sequence 50kg, 333kg of dichloromethane (1g / 5mL), 13kg of p-toluenesulfonic acid (1g / 0.25g), tempe...

Embodiment 2

[0037] Embodiment 2: A kind of preparation 7-bromo-1-heptene The method is characterized in that the specific preparation steps are as follows:

[0038] (1) Ring-opening reaction: Add 150kg of main raw materials tetrahydrofuran and 24kg (0.1eq) of trifluoroacetic acid to a 1000L reactor in sequence, control the temperature of the system at 10±2°C, and slowly add 525kg (1.5eq) of 48% hydrobromic acid aqueous solution dropwise ), after dropping, raise the temperature to 90±2°C, keep it warm for 4 hours, after the reaction is completed, cool down to 5±2°C, use 44kg (0.2eq) of sodium carbonate to adjust the pH to 7~8, extract, wash the organic phase, concentrate, The oily product 4-bromo-1-butanol was obtained 181kg, yield 56.8%, gas chromatography purity (GC): 96.5%;

[0039] (2) Hydroxyl protection: add the main raw material 4-bromo-1-butanol to the 500L reactor in sequence 35kg, N,N-dimethylformamide 263kg (1g / 8mL), imidazole 35kg (1g / 1g), temperature control 25±2°C, drop...

Embodiment 3

[0043] Embodiment 3: A kind of preparation 7-bromo-1-heptene The method is characterized in that the specific preparation steps are as follows:

[0044] (1) Ring-opening reaction: Add 100kg of main raw materials tetrahydrofuran and 4.8kg (0.02eq) of p-toluenesulfonic acid to a 500L reactor in sequence, control the temperature of the system at -5±2°C, and slowly add 117kg of 48% hydrobromic acid aqueous solution dropwise (0.5eq), after dripping, raise the temperature to 70±2°C, keep it warm for 1h, after the reaction is completed, lower the temperature to -5±2°C, use 7kg (0.05eq) of potassium bicarbonate to adjust the pH to 7~8, extract, organic phase Washing, concentration, the oily product 4-bromo-1-butanol is obtained 134kg, yield 63.3%, gas chromatography purity (GC): 96.0%;

[0045] (2) Hydroxyl protection: add the main raw material 4-bromo-1-butanol to the 500L reactor in sequence 70kg, methyl tert-butyl ether 104kg (1g / 2mL), triethylamine 7kg (1g / 0.1g), temperature...

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Abstract

The invention provides a method for preparing 7-bromine-1-heptylene. The method includes selecting a commercial raw material in markets or tetrahydrofuran prepared easily as a raw material; and carrying out ring opening, hydroxyl group protecting, coupling reaction, deprotection and substation reaction to obtain a target 7-bromine-1-heptylene product. The method has the advantages that the raw material is easy to obtain, reaction purity and yield are high, technological conditions are stable, operation is simple, cost is low, the method is environment-friendly and applicable to large-scale production, and the method is a new idea for preparing the 7-bromine-1-heptylene.

Description

(1) Technical field: [0001] The invention relates to a synthesis method of heptene derivatives, in particular to a method for preparing 7-bromo-1-heptene. (2) Background technology: [0002] Heptene derivatives are important intermediates in organic synthesis, and are widely used in the fields of medicine, pesticides, food additives, flavors and fragrances, synthesis of new materials, and development of fine chemicals. [0003] In the field of medicine, heptene derivatives play a vital role in the synthesis of pain, anti-inflammatory and sedative drugs. For example, protriptyline (commonly known as alanine, protriptyline) has both sedative and Some excitatory effects, and the antidepressant effect is relatively fast; in the field of pesticides, it is used for the preparation of high-efficiency and low-toxicity herbicides and insecticides, such as heptenylphos, which is used to control harmful organisms that endanger agricultural and animal husbandry production ( pests, mite...

Claims

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Application Information

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IPC IPC(8): C07C21/14C07C17/00
Inventor 洪浩詹姆斯・盖吉陈朝勇李常峰
Owner ASYMCHEM LAB TIANJIN
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