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Preparation method of diaryl acetylene compounds

A diaryl acetylene and compound technology, applied in the field of preparation of organic compounds, can solve the problems of few applicable objects, low yield, and side reactions in reductive coupling reactions, and achieve variable structure, convenient synthesis, and mild synthesis conditions Effect

Inactive Publication Date: 2018-04-24
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The defects of the above-mentioned technology mainly include: the elimination reaction is prone to side reactions, and the yield is not high; Carbon-carbon triple bond; few suitable candidates for reductive coupling reactions, and most reactions do not yield high yields

Method used

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  • Preparation method of diaryl acetylene compounds
  • Preparation method of diaryl acetylene compounds
  • Preparation method of diaryl acetylene compounds

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0045] (1) Preparation of raw materials

[0046] All gem-tribromomethyl arene compounds can be prepared by existing common synthesis methods, and the molecular structure of the gem-tribromomethyl arene compounds used in the examples is shown in the following formula.

[0047]

[0048] Raw compound abbreviation

R 1

R 2

R 3

1a

H-

H-

H-

1b

F-

H-

H-

1c

Cl-

H-

H-

1d

Br-

H-

H-

1e

H-

Cl-

H-

1f

H-

Br-

H-

1g

H-

CH 3 O-

H-

1h

H-

CH 3 C(O)-

H-

1i

H-

H-

F-

1j

H-

H-

Cl-

1k

H-

H-

Br-

1l

H-

H-

tert-C 4 h 9 -

1m

H-

H-

-CF 3

1n

H-

H-

-CN

1p

H-

H-

CH 3 C(O)-

1q

H-

H-

CH 3 OC(O)-

1r

H-

H-

-NO 2

[0049] (2) Synthesis method

[0050] Deoxidize a certain stoichiometric ratio of gem-tribromomethyl...

Embodiment 1 3

[0057] The synthesis of embodiment 1 tribromotoluene (1a)

[0058] Add 9.2 grams of toluene (0.1mol), 58.7 grams of NBS (0.33mol), 4.0 grams of BPO (0.017mol) and 300mL of CCl in a 500mL three-necked flask 4 , through nitrogen for 10 minutes. Heated to reflux, and stopped the reaction after 5 hours of reaction. The filtrate obtained after filtration was concentrated to obtain the crude product. The pure product 20.7 g of 1a was obtained by flash chromatography (petroleum ether). Yield 63%. 1 H NMR (400MHz, CDCl 3 ):δ8.03-8.00(m,2H),7.43-7.38(m,2H),7.36-7.32(m,1H). 13 C NMR (101MHz, CDCl 3 ):δ147.07,130.25,128.18,126.61,36.45.GC-MS(EI,m / z):249[M-Br] + .Anal.Calcd.for C 7 h 5 Br 3 : C, 25.57; H, 1.53. Found: C, 25.51; H, 1.51.

Embodiment 2

[0060] Example 2 Synthesis of o-fluorobenzotribromotoluene (1b), using o-fluorotoluene as raw material, yield 76%. 1 H NMR (400MHz, CDCl 3 ,ppm):δ6.85-6.91(m,2H),7.04-7.31(m,2H), 13 C NMR (101MHz, CDCl 3 ): δ30.93,117.31,123.24,128.44,132.73,133.40,159.19.GC-MS(EI,m / z):346[M + ].Anal.Calcd.for C 7 h 4 Br 3 F: C, 24.24; H, 1.16. Found: C, 24.20; H, 1.13.

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Abstract

The invention relates to preparation of an organic compound, and aims to provide a preparation method of diaryl acetylene compounds. The preparation method includes steps of adding associated tribromomethylarene compound and copper in a reactor to perform deoxidizing treatment; dissolving polyamine in a proper amount of anhydrous and oxygen-free solvent, and then adding to the reactor; performingcoupling reaction at 30-80DEG C for 3-12 hours; separating and purifying to obtain diaryl acetylene compounds. The preparation is gentle in synthesis condition and the reaction has good compatibilityto different functional groups; the raw material associated tribromomethylarene compound is convenient to compound and has different substituent groups and variable structure; by adopting one raw material, high-quality product can be obtained through simple treatment, and the output is high; by adopting two different raw materials, the asymmetrical diaryl acetylene compound can be prepared.

Description

technical field [0001] The invention relates to the field of preparation methods of organic compounds, in particular to a new method for synthesizing diaryl acetylene compounds. Background technique [0002] The diarylethyne compound is shown in the following formula. Alkynes containing carbon-carbon triple bond functional groups are widely used in the fields of medicine and optoelectronic materials due to their linear rigid structure and structural characteristics rich in π electrons. [0003] [0004] In organic synthesis, there are different methods for the formation of carbon-carbon triple bonds, which can be divided into conversion from existing functional groups to carbon-carbon triple bonds and direct construction of carbon-carbon triple bonds. [0005] Elimination reactions are an important strategy to obtain carbon-carbon multiple bonds. A carbon-carbon triple bond can be obtained from a carbon-carbon single bond or a carbon-carbon double bond as a precursor th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/54C07C1/26C07C25/24C07C17/23C07C43/215C07C41/24C07C22/08C07C255/50C07C253/30C07C49/796C07C45/65C07C69/76C07C67/317C07C205/06C07C201/12C07C49/84
CPCC07C15/54C07C22/08C07C25/24C07C43/215C07C49/796C07C49/84C07C69/76C07C205/06C07C255/50C07C2531/22
Inventor 王齐任丽美
Owner ZHEJIANG UNIV
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