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Preparation method of 1-hydroxyl-1,2-benziodoxol-3(1H)-one

A technology of phenyliodide and hydroxyl, which is applied in the field of synthesis of hypervalent iodine reagents, can solve problems such as difficult storage, expensive pentavalent iodine reagents, explosiveness, etc., and achieve the effects of high selectivity, high yield, and mild reaction conditions

Inactive Publication Date: 2018-03-23
HUBEI UNIV OF TECH
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  • Description
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Problems solved by technology

However, pentavalent iodine reagents are expensive, difficult to store, and potentially explosive

Method used

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  • Preparation method of 1-hydroxyl-1,2-benziodoxol-3(1H)-one
  • Preparation method of 1-hydroxyl-1,2-benziodoxol-3(1H)-one

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Embodiment example 1、1

[0013] Implementation case 1, the preparation of 1-hydroxyl-1,2-phenyliodoacyl-3(1H)-ketone:

[0014]

[0015] Into a 250mL round bottom flask, add one No. 5 magneton, 10mmol o-iodobenzoic acid, 10mmol sodium periodate, 20mL glacial acetic acid, stir to completely dissolve the o-iodobenzoic acid, and reflux; the condenser tube flows from bottom to top at 25°C After condensing the water, carry out condensation and reflux, place the round-bottomed flask in a 120°C oil bath for magnetic stirring, and the magnetic stirring speed is 600 rpm / s. React for 4 hours in the dark; stop the reaction, add 50 mL of distilled water to dilute, and let stand to cool to room temperature, filter, collect the crude product, wash three times with 20 mL, 0 ℃ ice water and 20 mL of acetone, and dry in a dark place to obtain 2.45 g white 1-hydroxy-1,2-phenyliodo-3(1H)-one product, yield 93%.

[0016] Product H NMR 1 H NMR (400MHz, (CD3) 2 SO)δ8.06-7.95(m,3H); 7.86-7.84(m,1H); 7.73-7.69(m,1H). 1...

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Abstract

The invention relates to a preparation method of 1-hydroxyl-1,2-benziodoxol-3(1H)-one. O-iodobenzoic acid, sodium periodate and glacial acetic acid are sequentially added to a 250 mL round-bottom flask and stirred until o-iodobenzoic acid is completely dissolved, and then reflux is performed; after condensed water (at the temperature of 25 DEG C) is introduced into a condensation pipe from bottomto top, the round-bottom flask is put in an oil bath pan at the temperature of 120 DEG C, magnetic stirring is performed, and the mixture reacts in a dark place for 4 h; after the reaction ends, the mixture is left to stand to be cooled to the room temperature, distilled water is added, the mixture is filtered, a rough product is collected and washed with icy water and acetone three times, a product is air-dried in the dark place and a white product of 1-hydroxyl-1,2-benziodoxol-3(1H)-one is obtained. The preparation method has mild reaction conditions, is simple in the technological process and high in selectivity, has higher yield reaching 93% and is environmentally friendly. The prepared product can be applied to the field of organic synthesis and the like.

Description

technical field [0001] The invention relates to the synthesis of hypervalent iodine reagent, especially the preparation method of 1-phenylethynyl-1,2-phenyliodyl-3-one. Background technique [0002] Hypervalent iodide is a mild, selective and environmentally friendly oxidizing agent. The chemical properties and reactivity of hypervalent iodine compounds are very similar to those of some hypervalent metal oxidants, such as mercury Hg(II), chromium Cr(VI), thallium Tl(III), lead Pb(IV), etc., but they do not have the toxicity of hypervalent metals , very friendly to the environment. Considering the impact on the environment, these heavy metal oxidants are limited due to their high toxicity, serious metal waste, and cannot be used in industrial processes, especially in the synthesis of pharmaceuticals and pesticides. In some ligand exchange, ligand coupling, functional group conversion and reductive elimination reactions, organic hypervalent iodine compounds can also play a r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D347/00
CPCC07D347/00
Inventor 李栋肖祯乐强张谦
Owner HUBEI UNIV OF TECH
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