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Method for preparing boric acid ester based on anilinolithium compound

A technology for lithium anilide and compound, which is applied in the field of preparing boric acid ester based on lithium anilide compound, can solve the problems of high cost, difficult catalyst, high safety risk and the like, and achieves short reaction time, high reaction yield and high catalytic activity. Effect

Active Publication Date: 2021-01-01
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Existing hydroboration methods have significant disadvantages: LiAlH 4 and NaBH 4 The system security risk is very high, SmI 2 -H 2 O-Et 3 The N system needs a lot of reagents in excess, and the transition metal complex system needs to be carried out under high temperature and high pressure. On the one hand, it needs to use a catalyst that is difficult to synthesize, and the cost is high; on the other hand, the catalytic reaction requires 60 o The reaction temperature of C and the reaction time of 24 hours

Method used

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  • Method for preparing boric acid ester based on anilinolithium compound
  • Method for preparing boric acid ester based on anilinolithium compound

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Embodiment one: Lithium anilide catalyzes the hydroboration reaction of benzoic acid and pinacol borane

[0024] Under an inert gas atmosphere, add benzoic acid (61.1 mg, 0.5 mmol) to the dehydrated and deoxygenated reaction flask, add pinacol borane (218 μL, 1.5 mmol) with a pipette gun, and finally add 40 μl Tetrahydrofuran solution (0.1M) of lithium anilide (0.8 mol% dosage, the same below), reacted at room temperature for 75 minutes, the reaction solution was exposed to air to terminate the reaction, and the solvent was removed under reduced pressure to obtain the product boric acid ester, which was decomposed by methoxy Phenylbenzene (84.15 mg, 0.5 mmol) was used as internal standard, and CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 H yield is 99%; 3 (THF) 2 , no product is obtained. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ) : δ7.20– 7.30 (m, 5H, ArH), 4.91 (s, 2H, CH 2 ), 1.24 (s, 36H, CH 3 ).

[0025] When the amoun...

Embodiment 2

[0031] Embodiment 2: Lithium anilide catalyzes the hydroboration reaction of 4-fluorobenzoic acid and pinacol borane

[0032] Under an inert gas atmosphere, add 4-fluorobenzoic acid (70.8 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (290 μL, 2 mmol) with a pipette gun, and finally add A THF solution of lithium anilide (0.8 mol% consumption) was reacted at room temperature for 75 minutes. mmol) as internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 H yield was 91%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ): δ7.20– 7.30 (m, 5H, ArH), 4.91 (s, 2H, CH 2 ), 1.24 (s, 36H, CH 3 ).

Embodiment 3

[0033] Embodiment three: Lithium o-methylanilide catalyzes the hydroboration reaction of 4-bromobenzoic acid and pinacol borane

[0034] Under an inert gas atmosphere, add 4-bromobenzoic acid (100 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (289 μL, 2 mmol) with a pipette gun, and finally add o- The tetrahydrofuran solution of methylanilinide lithium (0.8mol% consumption) was reacted at room temperature for 75 minutes, and the reaction solution was exposed to air to terminate the reaction, and the solvent was removed under reduced pressure to obtain the product boric acid ester. , 0.5 mmol) as internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 H yield was 93%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ): δ7.39 (br s, 2H, ArCH), 7.16 (t, 2H, ArCH), 4.80 (s, 2H, OCH 2 ), 1.19 (s, 36H,CH 3 ).

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Abstract

The invention discloses a method for preparing boric acid ester based on anilinolithium compound. Stir and mix the catalyst, borane and aromatic carboxylic acid in sequence, react for 35 to 45 minutes, expose to the air to terminate the reaction, remove the solvent from the reaction liquid under reduced pressure, and obtain boric acid esters with different substituents. The anilinolithium compound disclosed by the present invention can catalyze the hydroboration reaction of carboxylic acid and borane with high activity at room temperature, and the catalyst consumption is only 0.8mol% of the molar weight of carboxylic acid. Compared with the existing catalytic system, the use of The commercial reagent anilinolithium compound was discovered, the reaction conditions were mild, and the yield of borate esters with different substituents could reach 99% under limited conditions.

Description

technical field [0001] The invention relates to the application of the commercialized reagent anilinolithium compound, in particular to a method for preparing boric acid ester based on the anilinolithium compound. Background technique [0002] Organic borates can be regarded as orthoboric acid B(OH) 3 Derivatives in which the hydrogen in is replaced by an organic group, in addition to metaborate (ROBO) 3 . Due to its stability and low toxicity, borate is widely used in various fields, and it is a main raw material for the synthesis of boron-containing compounds. Boric acid ester compounds can not only be used as rust inhibitors, preservatives, polymer additives, anti-wear additives, automobile brake fluids, gasoline additives, flame retardants in cleaning agents, but also can be used as lubricating oil additives, etc. [0003] Existing hydroboration methods have significant disadvantages: LiAlH 4 and NaBH 4 The system security risk is very high, SmI 2 -H 2 O-Et 3 The...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/04
CPCC07F5/04B01J31/0252
Inventor 薛明强徐晓娟颜丹丹康子晗武振杰沈琪
Owner SUZHOU UNIV
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