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Method for preparing boric acid ester based on n-butyllithium

A technology of n-butyllithium and borate, which is applied in the field of preparation of borate based on n-butyllithium, can solve the problems of high cost, difficult catalyst, high safety risk, etc., achieve short reaction time, high reaction yield, Post-processing simple effects

Active Publication Date: 2020-09-08
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
On the one hand, the existing method 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 n-butyllithium
  • Method for preparing boric acid ester based on n-butyllithium

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Experimental program
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Effect test

Embodiment 1

[0023] Embodiment one: N-butyllithium 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 25 μL n-butyl Lithium tetrahydrofuran solution (0.1M) (0.5 mol% dosage, the same below), reacted at room temperature for 45 minutes, exposed the reaction solution to air, and removed the solvent to obtain the product borate, which was obtained by s-trimethoxybenzene (84.15 mg , 0.5 mmol) as internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 The yield of H is 97%; 3 (THF) 2 , no product is obtained. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ) : δ 7.22– 7.32 (m,5H, ArH), 4.92 (s, 2H, CH 2 ), 1.26 (s, 36H, CH 3 ).

Embodiment 2

[0029] Embodiment two: n-butyllithium catalyzed hydroboration reaction of benzoic acid and pinacol borane

[0030] Under an inert gas atmosphere, add benzoic acid (60.7 mg, 0.5 mmol) to the dehydrated and deoxygenated reaction flask, add pinacol borane (217 μL, 1.5 mmol) with a pipette, and finally add n-butyl The tetrahydrofuran solution of lithium (0.5 mol%) was reacted at room temperature for 20 minutes, the reaction solution was exposed to air, and the solvent was removed to obtain the product borate, with s-trimethoxybenzene (84.10 mg, 0.5 mmol) as the internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 H yield was 62%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ) : δ 7.21– 7.31 (m,5H, ArH), 4.92 (s, 2H, CH 2 ), 1.25 (s, 36H, CH 3 ).

Embodiment 3

[0031] Embodiment three: N-butyllithium catalyzes the hydroboration reaction of benzoic acid and pinacol borane

[0032] Under an inert gas atmosphere, add benzoic acid (59.9 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 n-butyl The tetrahydrofuran solution of lithium (0.5 mol% dosage) was reacted at room temperature for 45 minutes, the reaction solution was exposed to air, and the solvent was removed to obtain the product borate, with s-trimethoxybenzene (82.50 mg, 0.5 mmol) as the internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 H yield was 99%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ) : δ 7.21– 7.31 (m,5H, ArH), 4.92 (s, 2H, CH 2 ), 1.25 (s, 36H, CH 3 ).

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Abstract

The invention relates to application of n-butyl lithium, in particular to a method for preparing boric acid ester based on the n-butyl lithium. The method comprises the following steps: sequentially stirring a catalyst, borane and carboxylic acid, uniformly mixing and reacting for 40 to 50 minutes; exposing to the air for termination reaction; depressurizing reaction liquid and removing a solventto obtain the boric acid ester with different substituent groups. The n-butyl lithium disclosed by the invention can realize high-activity catalysis of hydroboration of carboxylic acid and borane at room temperature; the use amount of the catalyst is only 0.5 mol percent of the molar amount of carboxylic acid. Compared with an existing catalytic system, the boric acid ester utilizes a commercial reagent n-butyl lithium, and reaction conditions are mild; the yield of the boric acid ester with different substituent groups reaches 99 percent under limited conditions.

Description

technical field [0001] The invention relates to the application of the commercialized reagent n-butyl lithium, in particular to a method for preparing boric acid ester based on n-butyl lithium. 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 N system needs a lo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/04
CPCC07F5/04
Inventor 薛明强徐晓娟颜丹丹郑煜武振杰沈琪
Owner SUZHOU UNIV
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