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Method for preparing bromoacetonitrile from chloroacetonitrile

A technology of chloroacetonitrile and bromoacetonitrile, which is applied in the field of preparing bromoacetonitrile, can solve the problems of difficult treatment of strong acid waste liquid, low reaction yield, high sales price of bromoacetonitrile, etc.

Active Publication Date: 2022-05-17
沧州维智达美制药有限公司
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

The synthetic method of [0003] literature report comprises following several: 1) industrial preparation method adopts acetonitrile as raw material, and N-bromosuccinimide adds chlorination in solvent Carry out in carbon, and add a small amount of sulfur in the mixture, reflux reaction 14 hours, finally distill and make bromoacetonitrile, reaction yield is low, and can produce dibromoacetonitrile by-product (Journal of OrganicChemistry, 1953, vol.18, p.501,502); 2) the literature also reported that acetonitrile was used as raw material to react with 1-bromo-2,6-difluorobenzene or 1-bromo-2,-difluorobenzene to prepare bromoacetonitrile; 3) bromoacetamide As a raw material (Journal of general chemistry of the USSR, 1962, vol.32, p.890-894), under the action of phosphorus pentoxide, it is prepared by refluxing in a trimethylbenzene solvent. Phosphoric acid will be produced during the reaction, and the strong acidic waste liquid is not easy 4) take chloroacetonitrile as raw material, prepare bromoacetonitrile under the action of potassium bromide, but the yield is only 23% (HelveticaChimica Acta, 1971, vol.54, p. 2543-2551)
[0004] As mentioned above, there is low yield in the preparation method of existing report bromoacetonitrile, the problem such as reagent toxicity of use is big (carbon chloride), causes the sale of bromoacetonitrile The price is higher, so it is urgent to develop a method with simple method, high yield and meeting the requirements of industrial production

Method used

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  • Method for preparing bromoacetonitrile from chloroacetonitrile
  • Method for preparing bromoacetonitrile from chloroacetonitrile
  • Method for preparing bromoacetonitrile from chloroacetonitrile

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Add 10ml of acetonitrile, 2.00g of chloroacetonitrile, 3.27g of sodium bromide, and 0.39g (0.1eq) of sodium iodide into a 50ml single-necked bottle. Stir and heat up to reflux, and react for 5 hours. The content of bromoacetonitrile was 89%, the content of chloroacetonitrile was 10% by gas phase detection, and there were no other obvious impurities. After the reaction was completed, it was filtered, and the filtrate was concentrated under reduced pressure to recover the solvent, and then rectified under reduced pressure to separate the product to obtain bromoacetonitrile with a yield of 78%.

[0023] 1 H NMR(400MHz,Chloroform-d)δ3.78(s,2H).

[0024] Gas phase detection method:

[0025] Chromatographic column: DB-624 (30m×0.32mm, 1.8μm)

[0026] Column temperature: the initial column temperature is 50°C, rise to 200°C at 10°C / min, and keep for 10min

[0027] Injection port: 200°C

[0028] Detector: 220°C

[0029] Injection volume: 0.1μl

[0030] The test solution...

Embodiment 2

[0032] Sodium iodide dosage exploration

[0033] Experimental operation: Add 10mL of acetonitrile, 2.00g of chloroacetonitrile, 3.27g of sodium bromide, and different amounts of sodium iodide into a 50ml single-necked bottle. Stir and warm to reflux. Gas phase detection is carried out in different periods to detect the reaction process and impurity content (mass ratio). The results of the reactions under different conditions are shown in Table 1.

[0034] Table 1 different sodium iodide consumption prepares the reaction result of bromoacetonitrile

[0035]

Embodiment 3

[0037] Reaction solvent exploration: Add 2.00g of chloroacetonitrile, 3.27g of sodium bromide, and 0.08g of sodium iodide into a 50ml single-necked bottle, add 10mL of solvent, stir and raise the temperature to reflux, and react for 5 hours. The solvents investigated include methanol and ethanol, which are regularly sampled and analyzed by gas chromatography. The experimental results are shown in Table 2:

[0038] The reaction result of preparing bromoacetonitrile under the different solvent systems of table 2

[0039]

[0040]

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Abstract

The invention discloses a method for preparing bromoacetonitrile from chloroacetonitrile, and belongs to the field of chemical engineering. The method comprises the following steps: heating and refluxing chloroacetonitrile, inorganic bromide and an iodine-containing catalyst in a solvent, and purifying after the reaction is completed to obtain bromoacetonitrile. The easily available inorganic bromide is used as the bromine source, the used solvent is environment-friendly and recyclable, the reaction yield is greatly improved, the post-treatment method is simple, and the whole reaction route is clean and environment-friendly.

Description

technical field [0001] The invention relates to a method for preparing bromoacetonitrile by utilizing chloroacetonitrile, which belongs to the field of chemical industry. Background technique [0002] Bromoacetonitrile is an important intermediate in organic synthesis, widely used in the synthesis of many chemical products and pharmaceutical intermediates. For example, in the preparation route of the antiepileptic drug buvaracetam, bromoacetonitrile is an important intermediate raw material (patent EP3543229A1). In many synthetic studies, bromoacetonitrile is also an important source of cyanomethylene groups, which are used in the synthesis of complex compounds as potential amine groups, carboxyl groups or amides. [0003] The synthetic method of literature report comprises following several: 1) industrial preparation method adopts acetonitrile as raw material, carries out with N-bromosuccinimide in solvent plus carbon chloride, and adds a small amount of sulfur in the mixt...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C253/34C07C255/10
CPCC07C253/30C07C253/34C07C255/10
Inventor 瞿鑫马良
Owner 沧州维智达美制药有限公司
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