Halogenated Benzonitrile Alkoxide Nucleophilic Substitution Reaction And Cyano Phenol

Benzonitriles are very important sysnthetic intermediate and are used widely in the preparation of pharmaceuticals.dyes.pesticides and heterocyclic compounds,It is therefore important for the reaction of benzonitriles.In this dissertation Nucleophilic displacement reaction of halobenzonitrile and sodium alkoxide, sodium phenoxide, sodium acetaloxide has beendiscussed. Fristly 2,4-dicholobenzonitrile, 4-cholobenzonitrile, 4-bromobenzonitrile,4-fluorobenzonitrile have been synthesized through the reaction between 4-chlorobenzaldehyde, 4-bromobenzaldehyde, 4-fluorobenzaldehyde and hydrochlorohydroxylamine.2,4-fluorobenzonitrile have been synthesized through the reaction between 2.4-chlorobenzonitrile and anhydrous potassium fluoride .Secondly different alkoxybenzonitrile were prepared through the reaction2.4-difluorobenzonitrile and sodium methoxide ,ethoxide ,propoxide ,butoxide , phenoxide ,acetloxime in vavious solvents such as AlchoTHF,DMF.Then studied when them ethoxide:2,4-fluorobenzonitrile ratio was 1.3:land greater than 1:2 .A similar investigation of 2.4-chlorobenzonitrile with sodium methoxide ,ethoxide. phenoxide , acetloxime,have also been made in these three solvents systems .Then the reaction of o-and p-chlorobenzonitrile, p-bromobenzonitrile,p-fluorobenzonitrileand o-and p-chlorobenzotrifluoide with methoide in these three solvents were discussed .We have made the reaction of p-fluoroand p-bromobenzaldehyde with p-cholophenol and obtained compounds in good yields. At last we discussed the reaction of bromobenzene p-bromotoulene with sodium methoide in DMF system.At last 3-fluoro-4-cyanophenol was synthesized via the nucleophilic substitution of 2,4-difluorobenzonitrile and sodium methoxide ,followed by demethylation reaction of alkoxyfluorobenzonitrile to yield mixed phenols with aluminum trichloride ,and subsequently obtainted production throught sodium hydroxy solution ,then discussed the influcnece of temperature,catalyst,solvation.In the same way, p-cyanophenol. 5-fluoro-2-cyanophenol,dihydroxylbenzonitrile were synthesized .The the structures of the compounds were tested by IR, 'iTNMR^ HPLC and element analysis.The series of reaction introduced the activating powers of CN,CF3,CHO groups,Sohalobenzonitrile,chlorobenzontrifloride occur the nuclephilic displacement reaction easily. In aromatic nuclephilic substitution fluoride chloride bromide were displaced by various nuclephiles.Then we discussed the activating powers of different halo atom fluoride chloride bromide and nuclephiles and solvent and temperature to the influenece of reaction.