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One-pot Synthesis of Iodomethyltributyltin

A technology of tributyl tin iodide and n-butyl lithium, applied in the direction of tin organic compounds and the like, can solve the problems of difficult industrial production, long reaction period, harsh conditions, etc., and achieves easy commercial production, low production cost, and high product quality. A stable effect

Inactive Publication Date: 2018-03-09
成都安斯利生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The conditions for preparing Cu / Zn reagents are harsh and difficult to operate, and the purity of the prepared Cu / Zn reagents greatly affects the yield of subsequent target products
The reaction cycle is too long, and this method is not an ideal method for preparing iodomethyltributyltin from a synthetic point of view, and it is also difficult to realize industrial production

Method used

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  • One-pot Synthesis of Iodomethyltributyltin
  • One-pot Synthesis of Iodomethyltributyltin
  • One-pot Synthesis of Iodomethyltributyltin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In a 1L three-necked reaction flask, add diiodomethane (26.7g, 0.1mol), tributyltin chloride (32.5g, 0.1mol) and 200mL of anhydrous tetrahydrofuran, under nitrogen protection, cool to -78°C, slowly drop Add n-butyllithium (42mL, 0.11mol, 2.5M in hexanes), after the addition is complete, slowly warm up to room temperature, react for 12h, evaporate the solvent under reduced pressure with a rotary evaporator, then extract the product with 200mL of n-hexane, filter to remove Insoluble matter, remove solvent with rotary evaporator, generate pale yellow liquid, then underpressure distillation (140-142 ℃ / 1mmHg) obtains colorless liquid 29.3g, productive rate 68%, 1HNMR (CD 3 Cl): 1.94ppm, unimodal (2H); 1.56ppm, multimodal (6H); 1.46ppm, multimodal (6H); 1.05ppm, multimodal (6H); 0.97ppm, multimodal (9H).

Embodiment 2

[0031] In a 1L three-necked reaction flask, add diiodomethane (26.7g, 0.1mol), tributyltin chloride (32.5g, 0.1mol) and 200mL of anhydrous ether, under nitrogen protection, cool to -78°C, slowly drop Add n-butyllithium (42mL, 0.11mol, 2.5M in hexanes), after the addition is complete, slowly warm up to room temperature, react for 12h, evaporate the solvent under reduced pressure with a rotary evaporator, then extract the product with 200mL of n-hexane, filter to remove Insoluble matter, remove solvent with rotary evaporator, generate pale yellow liquid, then underpressure distillation (140-142 ℃ / 1mmHg) obtains colorless liquid 28g, productive rate 65%, 1HNMR (CD 3 Cl): 1.94ppm, unimodal (2H); 1.56ppm, multimodal (6H); 1.46ppm, multimodal (6H); 1.05ppm, multimodal (6H); 0.97ppm, multimodal (9H).

Embodiment 3

[0033] In a 10L three-necked reaction flask, add diiodomethane (1000g, 3.73mol), tributyltin chloride (1215.3g, 3.73mol) and 2L anhydrous tetrahydrofuran, under nitrogen protection, cool to -78°C, slowly drop n-Butyllithium (1567mL, 3.91mol, 2.5M in hexanes), after the addition, slowly warmed up to room temperature, reacted for 12h, evaporated the solvent with a rotary evaporator under reduced pressure, then extracted the product with 3L of n-hexane, filtered to remove the insoluble Substance, remove solvent with rotary evaporator, generate pale yellow liquid, then underpressure distillation (140-142 ℃ / 1mmHg) obtains colorless liquid 1012g, productive rate 63%, 1HNMR (CD 3 Cl): 1.94ppm, unimodal (2H); 1.56ppm, multimodal (6H); 1.46ppm, multimodal (6H); 1.05ppm, multimodal (6H); 0.97ppm, multimodal (9H).

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Abstract

The invention discloses a synthesis method of a medical intermediate iodomethyl tributyltin. The synthesis method specifically comprises the following steps: dropwise adding n-butyllithium to the raw materials including diiodomethane and tributyltin chloride at minus 78 DEG C to carry out in-situ reaction to generate the target product iodomethyl tributyltin. The method has the obvious advantages that the reaction raw materials are easy to obtain; the reaction operation is simple; large-scale production is easy to achieve; the yield is high; the purity is good; the production cost is low.

Description

technical field [0001] The invention relates to a new method for synthesizing a medical intermediate organotin, which belongs to the field of organic chemical synthesis, in particular to a new method for preparing iodomethyltributyltin. Background technique [0002] Organotin is an important class of pharmaceutical intermediates and organic chemical reagents. It is widely used in organic synthesis, especially through Stille coupling reaction, to form new C-C single bonds and construct some special functional groups. Sometimes organotins can form C-C bonds more efficiently than other coupling reagents such as organoboronic acids. Iodomethyl tributyltin is a very important organic building block in organic synthesis. After Stille reaction, an iodomethyl group can be constructed on small organic molecules, through which other subsequent group transformations can be performed. , so as to synthesize some useful drug small molecules. There are the following three methods in the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/22
Inventor 唐拥军莫珊刘玉琴
Owner 成都安斯利生物医药有限公司
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