Process to produce halo-4-phenoxyquinolines
A phenyl and alkyl technology, applied in the field of production of halo-4-phenoxyquinoline, can solve the problem that plants cannot grow effectively
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Embodiment 1
[0043] Example 1: Preparation of Fluoro-4-phenoxy-5,7-dichloroquinoline
[0044] Compound 3,5-dichloro aniline (DAC, 162.7g, 1.0mol) and diethylethoxymethylenemalonic acid (EMME, 221.1g, 1.02mol) were mixed into 1.135kg of recycled dodecylbenzene and 83.3g of fresh dodecylbenzene in alkylbenzenes. The reaction was carried out in a 3-liter stainless steel round-bottomed three-neck flask equipped with mechanical stirring and a Dean-Stark apparatus. The reaction mixture was stirred and flushed with nitrogen at a rate of 200 cc / min below the liquid surface. The reaction mixture was heated to 180°C and held for over 60 minutes, then to 200°C and held for 30 minutes, collecting approximately an aliquot of ethanol in the upper part of the Deck-Stark apparatus. The mixture was then cooled to room temperature and left overnight under nitrogen.
[0045] The reaction mixture was then heated to 240°C for approximately 7 hours while nitrogen was sparging at 180 cc / min subsurface and st...
Embodiment 2
[0048] Example 2: Preparation of halo-4-phenoxy-5,7-dichloroquinoline
[0049] This example illustrates steps 3-5 of the method. 7018 kg of wet (approximately 3% wt of water) sulfolane was charged to one reactor, followed by 906 kg of 3,5-dichloro-3-carboxy-4-hydroxyquinoline to form a wet slurry. The slurry was heated to 220°C at atmospheric pressure to remove most of the water and held at this temperature for 5 hours to produce 3,5-dichloro-4-hydroxyquinoline. The mixture was cooled to 105°C and full vacuum was applied for 3 hours to remove water. This mixture is then transferred to another reactor, and then 750 kg of sulfolane is used to flush the transfer pipe, and further cooled to 70° C., then 522 kg of thionyl chloride and 13.4 kg of N,N-dimethylformamide are added and 3,5-Dichloro-4-hydroxyquinoline was reacted at 75°C for 2 hours to produce 4,5,7-trichloroquinoline. The mixture was then heated to 95 °C and full vacuum was applied for 3 h to remove SO 2 and SOCl 2...
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