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The preparation method of novel 5-[4-(1-carboxynaphthyl)]-isophthalic acid
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A technology of isophthalic acid and dimethyl isophthalate, which is applied in the field of preparation of novel 5-[4-]-isophthalic acid, and achieves the effects of low synthesis cost, large specific surface area and high yield
Inactive Publication Date: 2017-11-07
ZUNYI MEDICAL UNIVERSITY
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[0023] The preparation method of 5-[4-(1-carboxynaphthyl)]-isophthalic acid of the present invention, synthetic steps are:
[0024] Take 4-bromo-naphthoic acid as raw material, react with thionylchloride to generate 4-bromo-naphthoyl chloride, then react with methanol to generate 4-bromo-naphthoic acid methyl ester (A), the synthetic route is as follows figure 2 shown. In addition, using 5-amino-dimethyl isophthalate as a raw material, bromine diazotization is substituted to generate 5-bromo-1,3-dimethyl phthalate (B), and B and biboronic acid pinacol ester Miyaura's boronate reaction generates 3,5-dimethoxycarbonylphenylboronic acid pinacol ester (C), and the synthetic route is as follows image 3 shown. Finally, compound A and C undergo a Suzuki coupling reaction to generate 5-[4-(1-methoxycarbonylnaphthyl)]-dimethyl isophthalate (D), and D is then hydrolyzed to obtain the target product 5-[4 -(1-Carboxynaphthyl)]-isophthalic acid (E), the synthetic route is as follows ...
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[0026] Ⅰ) If figure 2 Shown: Weigh 4-bromo-naphthoic acid (4.0 g, 16.0 mmol) in a 250 mL three-necked bottle, add 40 mLSOCl 2 , 5 drops of pyridine, reacted at 85 °C for 12 h, evaporated excess SOCl under reduced pressure 2 , cooled to normal temperature, 60mL methanol was added in a round-bottomed flask, and the reaction was heated at 85°C for 5 hours, and excess methanol was evaporated to obtain light yellow solid A (4.13 g), with a yield of 98%. Melting point: 374~375°C.
[0027] Compound A NMR 1 H NMR, 13 C NMR and high-resolution mass spectrometry data: 1 H NMR (400 MHz, CDCl 3 ) δ8.98–8.86 (m, 1H), 9.01–8.85 (m, 1H), 8.38–8.25 (m, 1H), 7.99 (d, J = 7.9 Hz,1H), 7.82 (d, J = 7.9 Hz, 1H), 7.74–7.56 (m, 2H), 4.00 (s, 3H). 13 C NMR (101MHz, CDCl 3 ) δ 167.45, 132.37, 132.16, 130.10, 128.89, 128.81, 128.49, 127.70, 127.62, 126.96, 126.23, 52.38. HRMS(ESI), C 12 h 19 BrO 2 , measured value (calculated value), m / z : 265.1023[M + ] (265.1027).
[0028] Ⅱ) If ...
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Abstract
The invention discloses a preparation method of novel 5-[4-(1-carboxyl naphthyl)]-isophthalic acid. 4-naphthoic acid is subjected to a methyl esterification reaction to generate a compound A 4-bromo-naphthoic acid methyl ester; 5-amino-dimethyl isophthalate is subjected to a diazotization bromination reaction to generate a compound B 5-bromo-dimethyl isophthalate; under the nitrogen protection condition, 5-bromo-dimethyl isophthalate and bis(pinacolato)diboron are subjected to a Miyaura boric acidesterification reaction by adding a catalyst to generate a compound C 3,5-dimethoxycarbonyl phenylboronic acidpinacol ester; the compound A and the compound C are subjected to a nitrogen protection reaction under the action of a catalyst to generate a compound D 5-[4-(1-methoxycarbonyl naphthyl)]-dimethyl isophthalate; the target compound E 5-[4-(1-carboxyl naphthyl)]-isophthalic acid is generated through a hydrolysis reaction, wherein the target compound E is shown as the following formula (please see the formula in the description). The method has the advantages of being simple in synthesizing method, low in synthesizing cost, and high in yield and product purity.
Description
technical field [0001] The invention relates to a preparation method of a rigid aromatic tricarboxylic acid ligand compound, in particular to a preparation method of novel 5-[4-(1-carboxynaphthyl)]-isophthalic acid. Background technique [0002] Rigid aromatic tricarboxylic acid ligands are widely used in the construction of MOFs materials. Such materials usually have good pore structure and large specific surface area, which make these materials suitable for energy gas storage and separation, catalysis, chemical sensing and pharmaceuticals. There are potential applications in different fields such as sustained release. For example, the Yaghi research group reported that a series of metal-organic framework materials with a large specific surface area were obtained by reacting a series of long-chain tricarboxylic acids with zinc salts, among which the BET specific surface area of MOF-210 is 6240 m 2 g -1 , the Langmuir specific surface area is as high as 10400 m 2 g -1 ...
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