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A method for synthesizing 5-methoxy-4-hydroxyl-2-formyl phenylboronic acid pinacol ester

A technology of aldehyde phenylboronic acid and pinacol ester, which is applied in the field of preparation of important pharmaceutical intermediates and achieves the effects of simple operation, readily available raw materials and low price

Active Publication Date: 2019-05-10
ABA CHEM CORP
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Problems solved by technology

[0004] In view of the problems referred to above, the purpose of this invention is to provide a method for synthesizing 5-methoxy-4-hydroxy-2-formyl phenylboronic acid pinacol ester, solving the problem of not being able to obtain synthetic 5-methoxy- TECHNICAL PROBLEMS OF 4-HYDROXY-2-ALPHENYLBORONIC ACID PINACOL ESTER

Method used

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  • A method for synthesizing 5-methoxy-4-hydroxyl-2-formyl phenylboronic acid pinacol ester
  • A method for synthesizing 5-methoxy-4-hydroxyl-2-formyl phenylboronic acid pinacol ester
  • A method for synthesizing 5-methoxy-4-hydroxyl-2-formyl phenylboronic acid pinacol ester

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Embodiment 1

[0048] Step 1: Synthesis of 4,5-dimethoxy-2-bromobenzaldehyde

[0049]3,4-dimethoxybenzaldehyde (100g, 0.602mol) shown in the following general formula 1 was dissolved in 600mL of methanol, the temperature of the solution was controlled at 15-20°C, and bromine (106g, 0.663mol ), after the dropwise addition, the solution was warmed up to 35-40°C and reacted for 24 hours. Continue to add 10% sodium thiosulfate aqueous solution (200mL, 0.126mol) dropwise, distill 200mL of methanol, then cool the solution to 10-15°C, stir for 2 hours, suction filter, and dry to obtain 130g of the following general formula 2 Light yellow solid 4,5-dimethoxy-2-bromobenzaldehyde, yield 89%.

[0050] 1 H NMR (400MHz, CDCl 3 )10.18(s,1H),7.41(s,1H),7.05(s,1H),3.95(s,3H),3.91(s,3H)

[0051]

[0052] Step 2: Synthesis of 5-Hydroxy-4-methoxy-2-bromobenzaldehyde

[0053] The 4,5-dimethoxy-2-bromobenzaldehyde (100g, 0.408mol) obtained by step 1 was added to 260mL 98% mass fraction of concentrated su...

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Abstract

The invention provides a method for synthesizing 5-methoxy-4-hydroxy-2-formylphenylboronic acid pinacol ester. The method particularly comprises the following steps: carrying out bromination on the raw material 3,4-dimethoxy benzaldehyde to obtain 3,4-dimethoxy-2-bromobenzaldehyde, carrying out demethylation to obtain 5-hydroxy-4-methoxy-2-bromobenzaldehyde, protecting hydroxyl with tert-butyl diphenyl silyl to obtain 5-tert-butyl-diphenylsiloxy-4-methoxy-2-bromobenzaldehyde, protecting formyl with glycerol acetal, reacting with triisopropyl borate under the action of butyl lithium to obtain 5-methoxy-4-tert-butyl-diphenylsiloxy-2-formylphenylboronic acid, removing the silyl protective group to obtain 5-methoxy-4-hydroxy-2-formylphenylboronic acid, and finally, carrying out esterification reaction on the 5-methoxy-4-hydroxy-2-formylphenylboronic acid and pinacol to obtain the target product 5-methoxy-4-hydroxy-2-formylphenylboronic acid pinacol ester. The method has the advantages of accessible raw materials, low cost and high yield, and can easily implement industrialization.

Description

technical field [0001] The invention belongs to the technical field of preparation of important pharmaceutical intermediates, and relates to a method for synthesizing 5-methoxy-4-hydroxyl-2-formyl phenylboronic acid pinacol ester, in particular to a method for synthesizing 5- Method of Methoxy-4-Hydroxy-2-Formyl Phenylboronic Acid Pinacol Ester. Background technique [0002] Coupling reaction is an important reaction to construct carbon-carbon bonds, and it has extremely important application value in the field of organic synthesis. Among the four classic coupling reactions Suzuki, Negeshi, Kumada, and Stille reactions, Suzuki coupling is the most widely used. Suzuki coupling refers to the cross-coupling of aryl or alkenyl boronic acid or boronate with chlorine, bromine, iodoarenes or alkenes under the catalysis of zero-valent palladium complex, and aryl or alkenyl boronic acid pinacol ester It is most commonly used because it is usually solid and very stable. Aryl or alk...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02
CPCY02P20/55
Inventor 石炜毛建勇周宇徐军
Owner ABA CHEM CORP
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