CN102531886A - Preparation method of 1-fluorin-6-iodo-benzoic acid - Google Patents
Preparation method of 1-fluorin-6-iodo-benzoic acid Download PDFInfo
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- CN102531886A CN102531886A CN 201010619259 CN201010619259A CN102531886A CN 102531886 A CN102531886 A CN 102531886A CN 201010619259 CN201010619259 CN 201010619259 CN 201010619259 A CN201010619259 A CN 201010619259A CN 102531886 A CN102531886 A CN 102531886A
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- benzoic acid
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Abstract
The invention provides a preparation method of 1-fluorin-6-iodo-benzoic acid. The 1-fluorin-6-iodo-benzoic acid is synthesized by taking 1-fluorin-6-iodo-methyl formate as a raw material and taking methanol as a solvent. The method has the advantages of reaction operability, easiness, practicability and industrial production application value.
Description
Technical field
The present invention relates to the fluorine chemical field, be specifically related to the compound method of 1-fluoro-6-iodo-benzoic acid.
Background technology
1-fluoro-6-iodo-benzoic acid is the midbody of agricultural chemicals and medicine, is a kind of pharmaceutical intermediate of bradykinin receptor antagonists, and it can also synthesize the medicine that can suppress certain antitumor drug spinoff, also is a kind of pharmaceutical intermediate of bradykinin receptor antagonists.Prior art needs reaction at low temperatures, and the condition of this type of reaction is harsh, and production cost is higher, is unfavorable for suitability for industrialized production.
Summary of the invention
The object of the present invention is to provide from the method for the synthetic 1-fluoro-6-iodo-benzoic acid of the initial catalysis of the reagent that is easy to obtain.Having now found that a kind of preparation method of 1-fluoro-6-iodo-benzoic acid, is raw material with 1-fluoro-6-iodo-benzoic acid methyl esters, and methyl alcohol is solvent, has synthesized 1-fluoro-6-iodo-benzoic acid.
Wherein, controlled temperature is 40 to 50 degrees centigrade in the reaction process.
Wherein, be controlled to be strong acidic environment in the reaction process.
According to batch mode, optional solvent, reactant and catalyzer are infeeded in the reactor drum.Be heated to the temperature that preceding text limit.Apply desirable pressure and maintenance.When reaction finishes, according to the solid/liquid separation technique of routine, preferably via filtration, separating catalyst.Reclaim the product that is obtained by routine, preferably perhaps pass through liquid/liquid extraction through distillation.
Embodiment
Provide below and be used to illustrate and nonrestrictive exemplary of the present invention.
In an embodiment, transformation efficiency is corresponding to the ratio of the substrate mole number that transforms with the substrate mole number that infeeds, and given yield is corresponding to the ratio of the product mole number that forms with the substrate mole number that infeeds.
Embodiment 1
Pour 350ml methyl alcohol and the above-mentioned 1-fluoro-of 164.2g (0.59mol) 6-iodo-benzoic acid methyl esters bullion under in the 1L four-necked bottle, stirring, the complete molten back of stirring drips and is dissolved in the solution that forms in the 200ml water by 35g (0.9mol), and the maintenance temperature of reaction is at 40 to 50 degrees centigrade; Tracking detects to raw material reaction complete, with separating out yellow particle shape solid after the Hydrogen chloride acidifying, washing; Dissolve back activated carbon decolorizing, acid out, cooling with 5% aqueous sodium hydroxide solution alkali; Crystallization; Dry the 145.0g white crystal, content 99.82% (through liquid chromatographic detection), productive rate 54.51%.
Embodiment 2
Pour 250ml methyl alcohol and the above-mentioned 1-fluoro-of 64.2g 6-iodo-benzoic acid methyl esters bullion under in the 1L four-necked bottle, stirring, the complete molten back of stirring drips and is dissolved in the solution that forms in the 200ml water by 25g, and the maintenance temperature of reaction is at 40 to 50 degrees centigrade; Tracking detects to raw material reaction complete, with separating out yellow particle shape solid after the Hydrogen chloride acidifying, washing; Dissolve back activated carbon decolorizing, acid out, cooling with 5% aqueous sodium hydroxide solution alkali; Crystallization; Dry the 45.0g white crystal, content 98.82% (through liquid chromatographic detection), productive rate 53.51%.
Embodiment 3
Pour 150ml methyl alcohol and the above-mentioned 1-fluoro-of 14.2g 6-iodo-benzoic acid methyl esters bullion under in the 1L four-necked bottle, stirring, the complete molten back of stirring drips and is dissolved in the solution that forms in the 200ml water by 15g, and the maintenance temperature of reaction is at 40 to 50 degrees centigrade; Tracking detects to raw material reaction complete, with separating out yellow particle shape solid after the Hydrogen chloride acidifying, washing; Dissolve back activated carbon decolorizing, acid out, cooling with 5% aqueous sodium hydroxide solution alkali; Crystallization; Dry the 15.0g white crystal, content 97.62% (through liquid chromatographic detection), productive rate 52.71%.
Claims (3)
1. the preparation method of a 1-fluoro-6-iodo-benzoic acid is characterized in that, is raw material with 1-fluoro-6-iodo-benzoic acid methyl esters, and methyl alcohol is solvent, has synthesized 1-fluoro-6-iodo-benzoic acid.
2. the method for claim 1 is characterized in that, controlled temperature is 40 to 50 degrees centigrade in the reaction process.
3. the method for claim 1 is characterized in that, is controlled to be strong acidic environment in the reaction process.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010619259 CN102531886A (en) | 2010-12-31 | 2010-12-31 | Preparation method of 1-fluorin-6-iodo-benzoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010619259 CN102531886A (en) | 2010-12-31 | 2010-12-31 | Preparation method of 1-fluorin-6-iodo-benzoic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102531886A true CN102531886A (en) | 2012-07-04 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201010619259 Pending CN102531886A (en) | 2010-12-31 | 2010-12-31 | Preparation method of 1-fluorin-6-iodo-benzoic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102531886A (en) |
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2010
- 2010-12-31 CN CN 201010619259 patent/CN102531886A/en active Pending
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Legal Events
| Date | Code | Title | Description |
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| DD01 | Delivery of document by public notice |
Addressee: Shanghai Sinofluoro Scientific Co., Ltd. Document name: Notification of Passing Preliminary Examination of the Application for Invention |
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| C06 | Publication | ||
| PB01 | Publication | ||
| DD01 | Delivery of document by public notice |
Addressee: Shanghai grace Technology Co., Ltd. Jiang Jing Document name: Notification of Publication of the Application for Invention |
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| DD01 | Delivery of document by public notice |
Addressee: Jiang Jing Document name: Notification of before Expiration of Request of Examination as to Substance |
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| DD01 | Delivery of document by public notice |
Addressee: Jiang Jing Document name: Notification that Application Deemed to be Withdrawn |
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| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20120704 |