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Synthesis method for 3-bromine-4-(methylol)methyl benzoate

A technology of methyl aldehyde methyl benzoate and methyl benzoate, which is applied in the field of synthesis of methyl 3-bromo-4-benzoate, can solve the problems of high toxicity, long reaction time, difficult purification and the like, and avoids light exposure. The reaction and synthesis process are safe and reliable, and the effect of simplifying the reaction process and post-processing process

Inactive Publication Date: 2015-12-30
SHANGHAI RAINBOW CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This synthetic method requires tetrabromine substitution, photoreaction is required, the whole reaction requires special equipment, and the reaction time is long and difficult to purify; and diazomethane is used in the reaction process, which is very toxic and explosive. On-site preparation is required in the room, and there is a great potential safety hazard

Method used

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  • Synthesis method for 3-bromine-4-(methylol)methyl benzoate
  • Synthesis method for 3-bromine-4-(methylol)methyl benzoate
  • Synthesis method for 3-bromine-4-(methylol)methyl benzoate

Examples

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Effect test

Embodiment 1

[0026] Add 250g of 3-bromo-4-methylbenzoic acid and 475g of NBS into a 3L three-necked flask, add 2.5L of carbon tetrachloride and 11g of benzoyl peroxide, heat up to 80 degrees and reflux for 2 days, cool to room temperature, filter, and use for cake filtering 2L of carbon tetrachloride was washed three times, and the combined filtrate was spin-dried to obtain about 220 g of crude 3-bromo-4-(dibromomethyl)benzoic acid, which was directly put into the next reaction.

[0027] Add 220g of the above-mentioned prepared 3-bromo-4-(dibromomethyl)benzoic acid crude product in a 3L three-necked flask, add 1.5L ethanol to dissolve, heat up 50 degrees, add dropwise 300ml aqueous solution of 200g silver nitrate, and keep warm for 55 React for 1 hour, cool to room temperature, filter, wash the filter cake three times with 1L ethanol, combine the filtrate and spin dry to obtain about 130g of crude product, the crude product is beaten with 500mL petroleum ether, and filter to obtain about 11...

Embodiment 2

[0031] Add 250g of 3-bromo-4-methylbenzoic acid and 475g of NBS into a 3L three-necked flask, add 2.5L of carbon tetrachloride and 11g of AIBN, heat up to 80 degrees for reflux reaction for 2 days, cool to room temperature, filter, filter the cake with 2L of carbon tetrachloride After washing three times, the combined filtrate was spin-dried to obtain about 210 g of crude product 3-bromo-4-(dibromomethyl)benzoic acid, which was directly put into the next step reaction.

[0032] Add 210 g of the 3-bromo-4-(dibromomethyl) benzoic acid crude product prepared above in a 3 L three-necked flask, add 1.4 L ethanol to dissolve, heat up 50 degrees, add dropwise 300 ml aqueous solution of 200 g silver nitrate, and keep warm for 55 React for 1 hour, cool to room temperature, filter, wash the filter cake three times with 1L ethanol, combine the filtrate and spin dry to obtain about 125g of crude product, use 500mL petroleum ether to beat the crude product, filter to obtain about 110g of 3-...

Embodiment 3

[0036] Add 250g of 3-bromo-4-methylbenzoic acid and 475g of NBS to a 3L three-necked flask, add 2.5L of carbon tetrachloride and 1.1g of AIBN, heat up to 80 degrees and reflux for 2 days, cool to room temperature, filter, filter the cake with 2L of tetrachloride The carbon was washed three times, and the combined filtrate was spin-dried to obtain about 200 g of crude product 3-bromo-4-(dibromomethyl)benzoic acid, which was directly put into the next step reaction.

[0037]Add 200 g of the 3-bromo-4-(dibromomethyl) benzoic acid crude product prepared above in a 3 L three-necked flask, add 1.3 L ethanol to dissolve, heat up 50 degrees, add dropwise 300 ml aqueous solution of 190 g silver nitrate, and keep warm for 55 reaction for 1 hour, cooled to room temperature, filtered, and the filter cake was washed three times with 1L ethanol, and the combined filtrate was spin-dried to obtain 125g of crude product, which was beaten with 500mL petroleum ether, and filtered to obtain about ...

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Abstract

The invention discloses a synthesis method for 3-bromine-4-(methylol)methyl benzoate. The method includes the steps of generating an intermediate 3-bromine-4-(bisbromomethyl)benzoic acid through a bromination reaction with methyl of easily-obtained 3-bromine-4-methyl benzoic acid as start raw materials, generating 3-bromine-4-aldehyde benzoic acid through 3-bromine-4-(bisbromomethyl)benzoic acid under the effect of silver nitrate, and conducting esterification and reduction to obtain 3-bromine-4-(methylol)methyl benzoate. The total recovery is about 30%.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to a synthetic method of 3-bromo-4-(hydroxymethyl)benzoic acid methyl ester. Background technique [0002] Methyl 3-bromo-4-(hydroxymethyl)benzoate is a white solid with a CAS number of 90326-62-8, and it is an important pharmaceutical intermediate. The synthetic method reported in the literature is to carry out tetrabromination of two methyl groups by NBS from 2,5-dimethylbromobenzene as a raw material, hydrolyze into 2-bromoterephthalaldehyde, and disproportionate to generate 3-bromo-4-( Hydroxymethyl) benzoic acid, reacted with diazomethane to obtain the target product (JournalofOrganicChemistry; vol.29; (1964); p.2034-2036). This synthetic method requires tetrabromine substitution, photoreaction is required, the whole reaction requires special equipment, and the reaction time is long and difficult to purify; and diazomethane is used in the rea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/31C07C69/78
CPCC07C51/363C07C51/373C07C67/08C07C67/31C07C69/78C07C65/30C07C63/70
Inventor 王西刘文兵徐代旺
Owner SHANGHAI RAINBOW CHEM
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