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Preparation method and device for iodobenzene dibenzoate derivative

A technology of dibenzoic acid and iodobenzene diacetate is applied in the field of preparation of iodobenzene dibenzoate derivatives, can solve problems such as difficult removal, environmental pollution of chlorobenzene, lower reaction yield and the like, and achieves good reactivity and oxidation The effect of stability, simple process and mild reaction conditions

Inactive Publication Date: 2017-01-04
HUBEI UNIV OF TECH
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Problems solved by technology

Strong acid oxides are dangerous to use, not easy to transport and store, and have a narrow scope of application
However, the oxidation effect of some inorganic metal salts is poor, and the application range of metal oxides and peroxides is wide, and they do not have environmental protection.
However, with the continuous development of organic synthesis, traditional oxidants are not enough to meet the practicability of different reactions, so it is of great significance to find an efficient and clean oxidant in organic synthesis, especially in transition metal catalysis
[0004] The preparation method of existing iodobenzene dibenzoate derivatives is mainly to synthesize iodobenzene dibenzoate with iodobenzene diacetate and benzoic acid with chlorobenzene as solvent, yet chlorobenzene has a higher boiling point and is difficult to remove after the reaction. Just cause product to be more difficult to separate out, reduced reaction yield, and when using chlorobenzene as solvent, this method is not applicable to the preparation of aliphatic iodobenzene, and chlorobenzene also has certain pollution to environment

Method used

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  • Preparation method and device for iodobenzene dibenzoate derivative
  • Preparation method and device for iodobenzene dibenzoate derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1, iodobenzene dibenzoate

[0021] Preparation of:

[0022] First add 6 mmol of iodobenzene diacetate, 12 mmol (2 equiv) of benzoic acid, and 5 ml of methanol as a solvent in a 25 mL round-bottomed flask until all benzoic acid and iodobenzene diacetate are dissolved in methanol; place the round-bottomed flask on a rotary evaporator Heat to 45°C and react for 0.5h; after the reaction, distill under reduced pressure and spin dry the solvent, and a large amount of white solid can be seen to precipitate; pour the solid obtained from the reaction liquid into a Buchner funnel, add 15ml of methanol to wash three times, and leave the remaining white solid in the air Dry; That is, iodobenzene dibenzoate. The yield was 86%.

[0023] H NMR 1 H NMR (400MHz, CDCl 3 ): δ7.37(t, J=7.64Hz, 4H), 7.47-7.57(m, 4H), 7.60-7.65(m, 1H), 7.93(d, J=7.64Hz, 4H), 8.24(d, J = 7.64Hz, 2H); 13 C NMR (100MHz, CDCl 3 ): δ122.3, 128.2, 130.1, 130.2, 131.0, 131.7, 132.5, 134.9, 171.3...

Embodiment 2

[0024] Embodiment 2, two (4-methoxybenzoic acid) iodobenzene

[0025] Preparation of:

[0026] In a 25mL round bottom flask, first add 6mmol of iodobenzene diacetate, 12mmol (2equiv) of 4-methoxybenzoic acid, and add 5ml of methanol as a solvent until all 4-methoxybenzoic acid and iodobenzene diacetate are dissolved in methanol; Place the round-bottomed flask on a rotary evaporator and heat it to 45°C for 0.5 hours; after the reaction, distill under reduced pressure and spin the solvent to dryness, and a large amount of white solids can be seen to precipitate; pour the solids obtained from the reaction solution into a Buchner funnel, and add 15ml of methanol was washed three times, and the remaining white solid was air-dried to obtain bis(4-methoxybenzoic acid)iodobenzene with a yield of 82%.

[0027] Bis(4-methoxybenzoic acid)iodophenyliodobenzenehydrogen NMR 1 H NMR (400MHz, CDCl 3 ): δ3.83(s,6H),6.85(d,J=8.88Hz,4H),7.53(t,J=7.84Hz,2H),7.59-7.63(m,1H),7.88(d,J= 8.84Hz,...

Embodiment 3

[0028] Embodiment 3, two (4-methylbenzoic acid) iodobenzene

[0029] Preparation of:

[0030] In the 25mL round bottom flask, add iodobenzene diacetate 6mmol earlier, 4-methoxybenzoic acid 12mmol (2equiv), add 5ml methyl alcohol as solvent until 4-methylbenzoic acid and iodobenzene diacetate are all dissolved in methanol; Place the round-bottomed flask on a rotary evaporator and heat it to 45°C for 0.5 hours; after the reaction, distill the solvent under reduced pressure and spin it dry, and a large amount of white solid can be seen to precipitate; pour the solid obtained from the reaction solution into a Buchner funnel, and add 15ml After washing with methanol three times, the remaining white solid was air-dried to obtain bis(4-methylbenzoic acid)iodobenzene with a yield of 85%.

[0031] H NMR 1 H NMR (400MHz, CDCl 3 ): δ2.37(s, 6H), 7.16(d, J=7.96Hz, 4H), 7.53(t, J=7.80Hz, 2H), 7.59-7.62(m, 1H), 7.82(d, J= 8.08Hz, 4H), 8.23(d, J=7.76Hz, 2H); 13 CNMR (100MHz, CDCl 3 )...

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Abstract

The invention relates to a preparation method and device for an iodobenzene dibenzoate derivative. The method includes the steps that 6 mmol of iodobenzene diacetate and 12 mmol of benzoic acid or a benzoic acid derivative or pivalic acid are added into a 25 mL round-bottom flask first, and 5 ml of methyl alcohol is added till benzoic acid or the benzoic acid derivative and iodobenzene diacetate are completely dissolved in methyl alcohol; the round-bottom flask is placed on a rotary evaporator to be heated to 45 DEG C for a reaction of 0.5 h; reduced pressure distillation is carried out to spin-dry the solvent, and it can be seen that a large amount of white solid matter is separated out; the reaction solution and obtained solid matter are poured into a Buchner funnel, the solid matter is washed with 15 ml of methyl alcohol three times, remaining white solid matter is aired, and the iodobenzene dibenzoate derivative is obtained, wherein the benzoic acid derivative is 4-methoxybenzoic acid or 4-methyl benzoic acid or 4-chlorobenzoic acid or 4-fluorobenzoic acid or 4-nitrobenzoic acid. By means of the preparation method and device, the reaction can be completed in one step, and the technological process is simple; conditions are mild, selectivity is high, environmental friendliness is achieved, and the yield is 72-95%.

Description

technical field [0001] The invention relates to a hypervalent iodine compound, especially a preparation method and device of iodobenzene derivatives of dibenzoate. Background technique [0002] Hypervalent iodine compounds have attracted much attention due to their many novel and unique reaction properties; in addition, they are environmentally friendly, simple to prepare, mild in nature, and high in reaction selectivity, so they are widely used in organic synthesis and transition metal catalyzed reactions, photo in the catalytic reaction. Among them, it is most commonly used as an oxidizing agent, such as alcohol oxidation, thioether oxidation, dearomatization and dehydrogenation reactions. Recently, there are some new applications, such as carbon-nitrogen bond formation reactions, peptide grafting reactions, etc. [0003] Traditional oxidants are mostly high-valent salts, strong acids or some metal cations. These oxidants have wide applicability, but most of them will cau...

Claims

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Application Information

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IPC IPC(8): C07C71/00C07C201/12C07C205/57
CPCC07C71/00C07C201/12C07C205/57
Inventor 李栋王阳张谦
Owner HUBEI UNIV OF TECH
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