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Preparation method of substituted iodobenzene with terminal double bonds

A terminal double bond, iodobenzene technology, applied in the field of preparation of substituted iodobenzene, can solve the problems of high price, difficult to obtain, etc., and achieves the effects of fast reaction speed, little environmental pollution, and simple operation

Pending Publication Date: 2022-03-01
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to overcome the above-mentioned technical deficiencies, propose a substituted iodobenzene with a terminal double bond and its preparation method, and solve the technical problems that substituted iodobenzene compounds with a terminal double bond are expensive and difficult to obtain in the prior art

Method used

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  • Preparation method of substituted iodobenzene with terminal double bonds
  • Preparation method of substituted iodobenzene with terminal double bonds
  • Preparation method of substituted iodobenzene with terminal double bonds

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preparation example Construction

[0016] The invention provides a method for preparing a substituted iodobenzene with a terminal double bond. The substituted iodobenzene with a terminal double bond has the following structural formula:

[0017]

[0018] In the formula, R 1 selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted benzyl, R 2 selected from methylene or carbonyl, R 3 Selected from F, Cl, Br, I, CN, NO 2 、CF 3 , COOEt, substituted or unsubstituted hydrocarbyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkyl, R 3 It can be monosubstituted or polysubstituted, and the position on the benzene ring is not limited.

[0019] The preparation method of the substituted iodobenzene with a terminal double bond comprises: using substituted o-iodoaniline and a compound containing a terminal double bond as starting materials to react in an organic solvent to obtain the substituted iodobenzene with a terminal double bond....

Embodiment 1

[0039] Example 1 N-allyl-N-benzyl-2-iodoaniline

[0040]

[0041] Add o-iodoaniline (50mmol) and benzaldehyde (50mmol) into the reaction flask, add 100mL of dichloroethane, then add acetic acid (100mmol) and sodium triacetoxyborohydride (150mmol), and the mixture reacts at room temperature 2 hours. After the reaction was completed, the reaction was quenched with water, extracted with dichloromethane, and the organic phases were combined and dried over anhydrous magnesium sulfate. The organic phase can be concentrated to obtain N-benzyl-2-iodoaniline. Add N-benzyl-2-iodoaniline (7mmol) to the reaction flask, add tetrahydrofuran 5mL, slowly add lithium diisopropylamide 8mL (1mol / L) at 0°C, and then add allyl bromide (14mmol) , the mixture was reacted for 2 hours and slowly raised to room temperature, and the reaction was monitored by TLC. After the reaction was completed, it was quenched with water. The organic phase was extracted with dichloromethane, combined and dried o...

Embodiment 2

[0044] Example 2 N-(2-iodophenyl)-acrylamide

[0045]

[0046] Add o-iodoaniline (10mmol) into the reaction flask, then add 5mL of dichloromethane, then add triethylamine (11mmol), then slowly add acryloyl chloride (11mmol) to the reaction solution dropwise, and the mixture is reacted at room temperature for 2 hours , the reaction was quenched with water after the reaction was complete. Extract with dichloromethane, combine the organic phases and dry with anhydrous magnesium sulfate, concentrate the organic phases to obtain N-(2-iodophenyl)-acrylamide with a yield of 75%. figure 2 It is the N-(2-iodophenyl)-acrylamide synthesized in Example 2 of the present invention 1 H NMR characterization spectrum.

[0047] 1 H NMR (200MHz, CDCl 3 ): δ (ppm) 8.27 (d, J = 8.0Hz, 1H), 7.72 (d, J = 8.0Hz, 1H), 7.52 (s, 1H), 7.66 (t, J = 8.0Hz, 1H), 6.79 (t,J=8.0Hz,1H),6.44-6.15(m,2H),5.76(d,J=10.0Hz,1H).

[0048] HRMS(ESI)m / z[M+H] + Calcd for C 9 h 9 INO(273.9723), found: 273.9729...

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Abstract

The invention discloses a preparation method of substituted iodobenzene with a terminal double bond, and the substituted iodobenzene with the terminal double bond has the following structural formula. Comprising the following steps: taking substituted o-iodoaniline and a compound containing terminal double bonds as initial raw materials, and reacting in an organic solvent to obtain substituted iodobenzene with terminal double bonds. The method disclosed by the invention is simple in preparation process, low in cost, high in reaction speed, simple to operate and small in environmental pollution, and a crude product does not need to be subjected to column chromatography separation; the substituted iodobenzene with the terminal double bonds can be subjected to a series of subsequent derivatization to obtain various forms of derivatives, so that natural products, medicines and bioactive molecules are prepared through subsequent derivatization reaction, and the substituted iodobenzene has important application value.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of substituted iodobenzene with terminal double bonds. Background technique [0002] Substituted iodobenzenes with terminal double bonds have important application value in organic synthesis. As important intermediates in organic synthesis, they can perform intramolecular Heck reactions, and can also perform intramolecular reactions with organometallic reagents of halogenated hydrocarbons. The cross-coupling reaction can also carry out its own free radical ring closure reaction under the action of a catalyst. For example, N-allyl-2-iodoaniline and its derivatives can undergo intramolecular Heck reaction to obtain indole compounds, and N-(2-iodophenyl)-acrylamide and its analogs are synthetic oxoindoles. Important precursors of indoles. Therefore, they can serve as important intermediates in the synthesis of natural products, pharmaceuticals, and b...

Claims

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Application Information

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IPC IPC(8): C07C209/10C07C211/52C07C231/02C07C233/15
CPCC07C209/28C07C209/10C07C231/02C07C211/52C07C233/15
Inventor 董志兵樊泳澔
Owner WUHAN INSTITUTE OF TECHNOLOGY
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