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Method for preparing aryl acetonitrile compound

A technology for aryl acetonitrile and compounds, applied in the field of compound synthesis, can solve problems such as environmental pollution and tin reagent toxicity

Active Publication Date: 2014-09-17
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the tin reagent used in this method is toxic and pollutes the environment.

Method used

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  • Method for preparing aryl acetonitrile compound
  • Method for preparing aryl acetonitrile compound
  • Method for preparing aryl acetonitrile compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Embodiment 1, preparation 2,6-dimethylphenylacetonitrile:

[0086] Reaction formula:

[0087]

[0088] The specific method is as follows: add 0.75 mmoles of potassium cyanoacetate in the vacuum reactor, and the molar amount is allyl palladium chloride (Pd) of 0.2% electrophilic substrate molar amount 2 (p-allyl) 2 Cl 2) Catalyst 0.01 millimole and electrophilic substrate molar consumption 0.6% S-Phos phosphine ligand 0.03 millimole, vacuumize, pass through high-purity argon, replace three times, add 0.5 millimole electrophilic substrate under the protection of argon flow 2,6-dimethylbromobenzene and solvent trimethylbenzene (the amount of solvent is added 2 milliliters of solvent per millimole of electrophilic substrate), placed at 140 ° C, after heating and stirring for 10 hours, decarboxylation according to the following method The reaction system after the coupling reaction is purified to obtain the target product 2,6-dimethylphenylacetonitrile: the reaction sy...

Embodiment 2

[0090] Embodiment 2, preparation benzyl nitrile:

[0091] Reaction formula:

[0092]

[0093] The method is the same as in Example 1, and the productive rate is shown in Table 1.

Embodiment 3

[0094] Embodiment 3, preparation benzyl nitrile:

[0095] Reaction formula:

[0096]

[0097] The method is the same as in Example 1, and the productive rate is shown in Table 1.

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Abstract

The invention provides a method for preparing an aryl acetonitrile compound, which obtaines an aryl acetonitrile compound by performing a decarboxylation coupling reaction of heating a decarboxylation coupling reagent and an electrophilic substrate in the presence of a palladium catalyst, a phosphine ligand, and an organic solvent. The method provided by the invention prevents the application of toxic reagents, and the reaction substrate is carboxylic acid or carboxylates, which is low in price, safe and stable, low in toxicity, and convenient for operation; the yield is high; the operation is easy; and the economy is good; compared with traditional synthetic methods reported before, the method has good compatibility for groups such as ester groups and carbonyls which are sensitive to alkali; the by-product is few; the atom economy is better than that of previous methods; the requirements for green chemistry are met; the catalytic amount is few; the catalytic efficiency is high; the separation is easy; the conversion rate is high; the yield is high; and the method has industrial and synthetic value.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a method for preparing aryl acetonitrile compounds. Background technique [0002] The traditional synthesis method of aryl acetonitrile compounds is to use benzyl halides and cyanides for nucleophilic substitution, but this method has low yields, uses highly toxic cyanides, and has relatively limited substrates. [0003] Currently, other methods reported include Palladium Catalyzed Reaction of ArylBromides with Cyanomethyltributyltin, Aromatic Cyanomethylation, Masanori KOSUGI, Masahiro ISHIGURO, Yoshikazu NEGISHI, HiroshiSANO, and Toshihiko MIGITA, CHEMISTRYLETTERS, pp.1511-1512, 1984. The method uses the tin reagent tributylacetonitrile stannane as a synthetic reagent, bromobenzene as an electrophilic substrate, palladium chloride as a catalyst, and tri-o-methylphenylphosphine as a phosphine ligand in the organic solvent m-xylene Heating at 120°C for 3 hours gave the product ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/00C07C253/30C07C255/33C07C255/37C07C255/35C07D317/60C07C255/41C07C303/30C07C309/73C07C255/51C07C319/20C07C323/62C07C255/40C07D295/192C07D333/24C07D215/12C07C255/46C07C57/58C07C51/08
Inventor 尚睿计东生傅尧郭庆祥刘磊
Owner UNIV OF SCI & TECH OF CHINA