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A method for preparing boric acid esters by non-catalyzed hydroboration of aromatic carboxylic acids

A technology for hydroboration of aromatic carboxylic acids, applied in the field of hydroboration of aromatic carboxylic acids, can solve problems such as excess, high cost, and high safety risks, and achieve high conversion rate, wide application range, and high yield Effect

Active Publication Date: 2020-06-16
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have obvious disadvantages: the LiAlH4 and NaBH4 systems have great safety risks, the SmI2-H2O-Et3N system requires a lot of excess reagents, and the Ru, Rh, Ir, Co transition metal complex systems need to be carried out under high temperature and high pressure.
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 a reaction temperature of 60oC and a reaction time of 24 hours

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment one: pinacol borane and benzoic acid 3:1 molar ratio generate borate

[0020] Under an inert gas N2 atmosphere, add benzoic acid (61.1 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (218 μL, 1.5 mmol) with a pipette gun, and react at room temperature After 12 hours, the reaction was removed from the glove box, and the reaction was terminated to obtain a boric acid ester, which was dissolved in CDCl3 with s-trimethoxybenzene (84.15 mg, 0.5 mmol) as an internal standard, stirred for 10 minutes, sampled, and NMR. The 1H yield was calculated to be 99%. NMR data of the product: 1H NMR (400 MHz, CDCl3): δ 7.22– 7.32 (m, 5H, ArH), 4.92 (s, 2H, CH2), 1.26 (s, 36H, CH3).

Embodiment 2

[0021] Embodiment two: pinacol borane and benzoic acid 4:1 molar ratio generate borate

[0022] Under an inert gas N2 atmosphere, add benzoic acid (60.3 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 react at room temperature After 6 hours, the reaction was removed from the glove box, and mes-trimethoxybenzene (83.05 mg, 0.5 mmol) was used as an internal standard, dissolved in CDCl3, stirred for 10 minutes, sampled, and NMR. The 1H yield was calculated to be 93%. NMR data of the product: 1H NMR (400 MHz, CDCl3): δ 7.22– 7.32 (m, 5H, ArH), 4.92 (s, 2H, CH2), 1.26 (s, 36H, CH3).

Embodiment 3

[0023] Embodiment three: pinacol borane and benzoic acid 4:1 molar ratio generate borate

[0024] Under an inert gas N2 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 react at room temperature After 12 hours, the reaction was removed from the glove box, and mes-trimethoxybenzene (82.50 mg, 0.5 mmol) was used as an internal standard, dissolved in CDCl3, stirred for 10 minutes, and sampled for NMR. The calculated 1H yield is 99%; NMR data of the product: 1H NMR (400 MHz, CDCl3): δ 7.22–7.32 (m, 5H, ArH), 4.92 (s, 2H, CH2), 1.26 (s, 36H, CH3).

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Abstract

The invention discloses a process for preparing boric acid ester by uncatalyzed hydroboration of aromatic carboxylic acid. According to the method, in an inert gas atmosphere, pinacol borane and carboxylic acid are uniformly mixed by stirring in a dehydrated and deoxidized reaction bottle, and reaction is carried out for 6-12 h to obtain boric acid ester; the carboxylic acid is benzoic acid, 4-bromobenzoic acid, 4-fluorobenzoic acid, 1-naphthoic acid, 2-methoxybenzoic acid and the like. According to the method, carboxylic acid is utilized to efficiently undergo hydroboration with borane in theabsence of a catalyst for the first time, so as to provide a new scheme for the preparation of the boric acid ester by hydroboration of a carbonyl compound and the borane.

Description

technical field [0001] The invention relates to the application field of green chemistry, in particular to the hydroboration reaction of aromatic carboxylic acid without solvent and catalyst. Background technique [0002] Organic boronic acid esters can be regarded as derivatives after the hydrogen in orthoboric acid B(OH)3 is replaced by organic groups, and there is also metaboric acid ester (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] The reduction catalytic system for the synthesis of boric esters reported in the literature is mainly the hydroboration of carboxylic acids catalyzed by L...

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康子晗武振杰沈琪
Owner SUZHOU UNIV
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