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A kind of preparation method of chlorobenzene Grignard reagent crystal product

A Grignard reagent, chlorophenyl Grignard technology, applied in the direction of magnesium organic compounds, etc., can solve the problems of potential safety hazards, troublesome liquid product transportation process, low yield of chlorophenyl Grignard reagent, etc., to achieve the promotion of reaction and the utilization of raw materials The effect of high efficiency and high product yield

Inactive Publication Date: 2018-08-07
邹城千禾生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current domestic production of chlorophenyl Grignard reagents generally adopts magnesium powder (shavings) and chlorobenzene as raw materials, and uses iodine as an initiator to synthesize, but the yield of chlorophenyl Grignard reagents prepared by this process is not high, and at the same time Liquid products are also more troublesome in the transportation process, so there are certain safety hazards and cannot meet the extensive needs of the current market

Method used

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  • A kind of preparation method of chlorobenzene Grignard reagent crystal product
  • A kind of preparation method of chlorobenzene Grignard reagent crystal product
  • A kind of preparation method of chlorobenzene Grignard reagent crystal product

Examples

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Embodiment 1

[0022] Example 1: Raw material molar ratio, 4-chloroanisole:magnesium chips=1:1.

[0023] (1) Preparation of Bromophenyl Grignard Reagent:

[0024] In a 250mL three-neck flask equipped with a water bath, mechanical stirring, thermometer and dropping funnel, add 2.00g (83.33mmol) of magnesium chips under anhydrous and anaerobic conditions, pass through dry nitrogen, add 0.13g (0.51 mmol) iodine, heated to the iodine vapor filled with the entire reaction flask, stop heating. 13.00g (82.80mmol) of bromobenzene was dissolved in 100mL of anhydrous ether and added dropwise to the above-mentioned reaction flask. First, a small amount was added dropwise, and slightly heated. After the reaction was triggered, the remaining mixed solution was slowly added dropwise (the drop rate was 3~4mL / min). After the dropwise addition, heat and reflux at 50°C for 1h, cool to room temperature, filter, and then prepare a saturated solution of diethyl ether, store at low temperature (-20°C to -25°C) ...

Embodiment 2

[0027] Example 2: Raw material molar ratio, p-methylchlorobenzene:magnesium chips=1:1.5.

[0028] (1) Preparation of 1,2-dibromoethane Grignard reagent:

[0029] In a 250mL three-neck flask equipped with a water bath, mechanical stirring, thermometer and dropping funnel, add 2.00g (83.33mmol) of magnesium chips under anhydrous and anaerobic conditions, pass through dry nitrogen, add 0.13g (0.51 mmol) iodine, heated to the iodine vapor filled with the entire reaction flask, stop heating. Dissolve 12.00g (63.87mmol) of 1,2-dibromoethane in 100mL of anhydrous ether and add it dropwise to the above-mentioned reaction flask. Solution (dropping rate is 3 ~ 5mL / min). After the dropwise addition, heat and reflux at 50°C for 1h, cool to room temperature, filter, and then prepare a saturated solution of diethyl ether, store it at low temperature (-20°C~-25°C), and block crystals will precipitate overnight, filter at low temperature 14.31 g of 1,2-dibromoethane Grignard reagent crysta...

Embodiment 3

[0032] Embodiment 3: Raw material molar ratio, chlorobenzene:magnesium chips=1:1.2.

[0033] (1) Preparation of 1,2-dibromoethane Grignard reagent: same as step (1) in Example 2.

[0034] (2) Preparation of chlorophenyl Grignard reagent:

[0035] Add 7.20g (300.00mmol) magnesium chips into a 500mL three-necked flask equipped with a water bath, mechanical stirring, thermometer and dropping funnel, feed dry nitrogen, and completely cover the magnesium chips with ether. Add 200mL of anhydrous ether and 28.14g (250.00mmol) of chlorobenzene into the constant pressure dropping funnel, and then dropwise into the reaction flask containing magnesium chips (the drop rate is 3-4mL / min). / 10 volume, add 0.34g (1.44mmol) BrMgCH 2 CH 2 For blocky crystals of MgBr, when the magnesium scraps start to be consumed gradually, continue to add the diethyl ether solution of chlorobenzene dropwise under stirring conditions (the drop rate is 4-5mL / min), heat slightly, and make the solution gradual...

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Abstract

The invention discloses a preparation method of a chlorobenzene Grignard reagent crystal product and belongs to the technical field of Grignard reagent preparation. The preparation method comprises preparing a bromobenzene Grignard reagent and a 1, 2-dibromoethane Grignard reagent, adding chlorobenzene and magnesium chips into anhydrous ether in a nitrogen protective atmosphere, adding bromobenzene Grignard reagent bulk crystals or 1, 2-dibromoethane Grignard reagent bulk crystals as initiators into the mixture, slowly heating the mixture until a backflow state, keeping the state for 2-4h to obtain a chlorobenzene Grignard reagent crude product, filtering the crude product, preparing an ether saturated solution from the chlorobenzene Grignard reagent-containing filtrate, storing the ether saturated solution at a low temperature of -20 to -25 DEG C for 48h so that a lot of bulk chlorobenzene Grignard reagent crystals are precipitated. The preparation method utilizes easily available raw materials, has simple processes, realizes a high utilization rate and a high yield and is suitable for industrial production.

Description

Technical field: [0001] The invention belongs to the technical field of Grignard reagent preparation, in particular to a method for preparing a low-cost, high-purity chlorophenyl Grignard reagent crystal product. Background technique: [0002] Grignard reagent is one of the most valuable and widely used chemical reagents in organic synthetic chemistry. Chlorophenyl Grignard reagent is also an important reagent for the preparation of alcohols, aldehydes, carboxylic acids and organometallic compounds with benzene and chlorophenyl groups. . In the initial research process, people mostly prepared Grignard reagents from active halogenated hydrocarbons. For halogenated aromatic hydrocarbons with poor activity, the reaction was difficult to initiate and the reaction was difficult to carry out. Generally, the yield of the product was low, and the application was also limited. greater restrictions. Nevertheless, the application of halogenated aromatic Grignard reagents is still rel...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F3/02
CPCC07F3/02
Inventor 张千峰马森李晓东贾爱铨
Owner 邹城千禾生物科技有限公司