Novel synthesis method for 5-[10-(9-carbosyl anthryl)]-isophthalic acid
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A technology of isophthalic acid and synthesis method, applied in the field of synthesis of novel 5-[10-]-isophthalic acid
Active Publication Date: 2016-01-13
ZUNYI MEDICAL UNIVERSITY
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[0024] The synthetic method of 5-[10-(9-carboxyanthracenyl)]-isophthalic acid of the present invention, synthetic steps are:
[0025] Using 5-amino-1,3-phthalic acid dimethyl ester as raw material, bromine diazotization is substituted to generate 5-bromo-1,3-phthalic acid dimethyl ester (A), A and diboronic acid pinacol ester Generate 3,5-dimethoxycarbonylphenylboronic acid pinacol ester (B) through coupling reaction, the synthetic route is as follows figure 2 shown. In addition, using 9-anthracenecarboxylic acid as a raw material, the bromination reaction produces 10-bromo-9-anthracenecarboxylic acid (C), and C reacts with thionyl chloride to form 10-bromo-9-anthracenecarbonyl chloride, which is then reacted with methanol to form 10 -Bromo-9-methyl anthracenecarboxylate (D), the synthetic route is as follows image 3 shown. Finally, compound B and D undergo a Suzuki coupling reaction to generate 5-[10-(9-methoxycarbonyl anthracenyl)]-dimethyl isophthalate (E), and E is th...
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[0027] (i) if figure 2Shown: Weigh 5-amino-1,3-phthalic acid dimethyl ester (10.0g, 47.6mmol) into a 500mL three-necked flask, slowly add hydrobromic acid solution (15%, 225mL) dropwise, after dropping, place on ice Cool the solution in a bath to 5°C, slowly add sodium nitrite solution (2.5M, 23mL) dropwise under rapid stirring, and slowly add CuBr (9.8g) in hydrobromic acid (45%, 90mL) solution dropwise to the three-necked flask to keep the reaction After the temperature was lower than 5°C, the mixture was stirred at room temperature for 2 hours, and the crude product was obtained by filtration. After drying, it was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=8 / 3) to obtain a white powder A (8.28g). Yield 63.4%. Melting point: 88~89℃.
[0028] Compound A NMR 1 HNMR, 13 CNMR and high-resolution mass spectrometry data: 1 HNMR (400MHz, CDCl 3 )δ8.59(s,1H),8.34(s,2H),3.95(s,7H). 13 CNMR (101MHz, CDCl 3 ) δ 164.78, 136.53, 132.12, 1...
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Abstract
The invention provides a novel synthesis method for 5-[10-(9-carbosyl anthryl)]-isophthalic acid. A diazotization bromination reaction is conducted on 5-amino-1,3-benzenedicarboxylic acid dimethyl ester to synthesize a compound A, namely, 5-bromine-1,3-benzenedicarboxylic acid dimethyl ester, and catalysts are added to 5-bromine-1,3-benzenedicarboxylic acid dimethyl ester under the condition of nitrogen protection to make 5-bromine-1,3-benzenedicarboxylic acid dimethyl ester react with bis(pinacolato)diboron so as to generate a compound B, namely, 3,5-bis(methoxycarbonylethyl)phenylboronic acid pinacol ester. In addition, anthracene-9-carboxylic acid is bromized to obtain a compound C, namely, 10-bromine-9-carboxylic acid, the compound C is subjected to methyl esterification to generate a compound D, namely, 10-bromine-9-anthracene methyl formate, and the compound D and the compound B are subjected to a nitrogen protection reaction under the effect of catalysts to generate a compound E, namely, 5-[10-(9-methoxycarbonyl group anthryl)]-benzenedicarboxylic acid dimethyl ester, and a target compound F, namely, 5-[10-(9-carboxyl anthryl)]-isophthalic acid through a hydrolysis reaction. The target compound F is shown in the figure.
Description
technical field [0001] The invention relates to a synthesis method of a rigid biaryltricarboxylic acid ligand compound, in particular to a synthesis method of novel 5-[10-(9-carboxyanthracenyl)]-isophthalic acid. Background technique [0002] Extended rigid tricarboxylic acid ligands are widely used in the synthesis of MOFs materials. These materials usually have good pore structure and large internal surface area, which make these materials suitable for gas storage, chemical sensing, catalysis and drug release. have potential applications in different fields. For example, a three-dimensional porous compound (HKUST-1) with ring-shaped binuclear copper as a secondary structural unit synthesized by trimesic acid and copper nitrate under hydrothermal conditions; a MOF with a qom topology network synthesized by a solvothermal method with zinc nitrate -177, [Zn 4 O(BTB) 2 ·(DMF) 15 (H 2 O) 3 ]. The compound has a specific surface area of 4500m 2 g -1 , has strong adsor...
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