108-70-3, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 108-70-3, name is 1,3,5-Trichlorobenzene, A new synthetic method of this compound is introduced below.
This is an example of the coupling addition of three aryl groups to a trichloro aromatic hydrocarbon by the catalyst of this disclosure. [0071] The 1 liter coupling reaction flask was equipped as described inexample 3. The flask was charged with anhydrous NiBr2 0.55 grams / 2.5 mmole, TPP 6.55 grams / 25 mmole; 1,3,5-trichlorobenzene 18.31 grams / 0.10 mole and 50 ml / 44.3 grams of reagent grade o-xylene. The green solution of the NiBr2/TPP catalyst was formed by heating the mixture to ref lux and holding at reflux for 30 minutes. After cooling to ambient temperature, 100 ml of dry THE solvent was added. The 500 ml pressure equalizing addition funnel was charged with 320 ml of 1 .0 molar 2-chloromagnesiumtoluenesolution in THE (Aldrich) 0.32 mole. This represents a 3.2/ 1 mole ratio of Grignard / trichloroaryl or about a 7 mole % excess of Grignard. A sample of the starting mixture was taken for gas chromatographic analysis (sample 1). [0072] The coupling reaction was carried out at 50 degrees Celsius by the dropwize addition of the Grignard reactant over 2 hours and 50 minutes.The addition of the Grignard solution turned the mixture to a red-brown color. The mixture was stirred an additional 2 hours at 50 degrees Celsius following the complete addition of the Grignard. Additional samples were taken at 41% of the Grignard addition (sample 2); immediately following the complete addition of Grignard (sample 3); after 2 hours of additional stirring (sample 4)and following the acid hydrogen peroxide quench (sample 5). The table below lists the amount in grams of a given material in the reaction flask on the basis of gas chromatographic analysis. Sample 5 was also submitted for GC-MS analysis for identification of the individual components. This analysis was unable to find any traces of the mono-arylation intermediate product, atestament to the efficiency of the catalyst of this disclosure to poly-arylate multihalogenated aromatic compounds. [0073] The crude product solution was treated with 35 ml of concentrated hydrochloric acid and 115 ml of deionized water, followed by the addition of 3 ml of 50% aqueous hydrogen peroxide. The two liquid phases were separated in a funnel and the yellow organic layer was washed with two 100 ml portionsof 1% aqueous NaCI solution. The organic layer was subjected to nitrogen stripping followed by vacuum at 0.5 kPa pressure while warming the flask to about 50 degrees Celsius to remove all the THE and most of the o-xylene. The sticky solid was dissolved in a mixture of 200 ml of isomeric hexane and 50 ml of toluene. This was passed through a 2.5 cm by 7.5 cm diameter bed ofBrockmann I alumina and the bed washed through with a total of 300 ml of a2/1 v/v mixture of isomeric hexane / toluene. The clear colorless filtrate was stripped with nitrogen to a white sticky waxy solid. This material was recrystallized from 100 ml of refluxing isomeric hexane and cooling to ambient temperature. The white crystals were washed with two 25 ml portions of coldisomeric hexane and dried under 0.5 kPa vacuum. The net weight of pure product was 21.14 grams representing 60% theoretical yield based on 1,3,5- trichlorobenzene.[0074] The proton NMR spectrum ppm relative to TMS: 3H (S) 7.31 ppm 2,4,6 aromatic C-H; 12H (overlapping doublets) 7.30-7.32 ppm aromatic C-Hon outside aromatic rings; 9H (S) 2.415 ppm benzylic CH3.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; EASTMAN CHEMICAL COMPANY; DEVON, Thomas, James; (41 pag.)WO2018/44824; (2018); A1;,
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