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Method for preparing halogenated allenes

A technology of substituted allene and brominated allene, which is applied in the preparation of halogenated hydrocarbons, chemical instruments and methods, organic chemistry, etc., can solve the problems of complex reaction operation, low reaction yield, poor selectivity, etc., and achieve easy operation of the reaction , post-processing is simple, no environmental pollution effect

Inactive Publication Date: 2009-03-18
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But, above method has following deficiency: (1) reaction yield is low, (2) selectivity is poor, usually obtains mixture, (3) uses poisonous halogenation reagent, (4) reaction operation is complicated, not easy to handle

Method used

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  • Method for preparing halogenated allenes
  • Method for preparing halogenated allenes
  • Method for preparing halogenated allenes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Step 1 Install a three-way nitrogen head on one side of the 50mL two-necked flask and connect it with ultra-pure nitrogen. Put a stirring magnet in the bottle and stopper it, and install the flask on a magnetic stirrer. The reaction flask was evacuated and filled with nitrogen and repeated three times. Then, follow up with the method for handling sensitive substances in the air.

[0018] Step 2 Add propargyl alcohol (1.0mmol), N-chlorosuccinimide (NCS, 1.55mmol), PPh 3 (1.5mmol), CH 2 Cl 2 (10 mL), stirred at 0°C for 1 hour.

[0019] Step 3 The solvent of the reaction solution obtained in Step 2 was evaporated, and the obtained crude product was purified by silica gel column chromatography using n-hexane as the eluent to obtain a pure product. The results are shown in Table 1.

Embodiment 2

[0021] Step 1 together with the example

[0022] Step 2 Add propargyl alcohol (1.0mmol), N-bromosuccinimide (NBS, 1.55mmol), PPh 3 (1.5mmol), CH 2 Cl 2 (10 mL), stirred at room temperature for 1 hour.

[0023] Step 3 Together with the example, the results are shown in Table 2.

Embodiment 3

[0025] Step 1 together with the example

[0026] Step 2 The temperature is 25°C, and the others are the same as the examples.

[0027] Step 3 together with the example

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Abstract

The invention provides a method for preparing halogenated allene, which belongs to the technical field of organic synthesis. The method is characterized in that an aromatic propargyl alcohol compound as a raw material reacts with N-chlorosuccinimide (NCS) or N-bromosuccinimide (NBS) as a halogenating reagent under the action of tricyclohexyl phosphine (PCy3), triphenylphosphine (PPh3), 1,4-bis(diphenylphosphino)butane (dppb), 1,2-bis(diphenylphosphino)ethane (dppe), bis(diphenylphosphino)methane (dppm), 1,3-bis(diphenylphosphino)propane (dppp) or 1,1'-bis(diphenylphosphino)ferrocene (dppf), ether, acetonitrile, tetrahydrofuran, dichloromethane, chloroform, toluene or 1,4 dioxane are taken as a solvent, at a reaction temperature of between 0 and 50 DEG C, so as to form chloro or bromo allene compound. The method has the advantages of simple operation, high selectivity, easy aftertreatment, medium yield and little pollution to environment, and is an ideal method for synthesizing the halogenated allene.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry and relates to a preparation method of chlorinated or brominated allenes, specifically using propargyl alcohol compounds as raw materials and N-chlorosuccinimide (NCS ) or N-bromosuccinimide (NBS) as a halogenating reagent, in the presence of trihydrocarbyl phosphine, a method for preparing chlorinated or brominated allene compounds. Background technique [0002] Halogenated allenes have high reactivity and can undergo various reactions such as substitution, oxidation, reduction, addition, polymerization, and Diels-Alder. They are important intermediates in organic synthesis and are widely used in organic synthesis. For example, the synthesis of halogenated furans, α, β-unsaturated ketones and some natural products. [0003] In the preparation method of reported halogenated allene, comprise: 1. in the presence of cuprous halide, prepare halogenated allene (Jacobs, T.L.; Brill,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C22/04C07C17/00
Inventor 包明杜欣冯秀娟戴耀何仁
Owner DALIAN UNIV OF TECH