Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: MichaelWestin on May 03, 2010, 12:30:32 AM

Title: Toluene to m-fluorotoluene (or 3-Fluortoluene) Synthesis
Post by: MichaelWestin on May 03, 2010, 12:30:32 AM

Can anybody give me a hand with the best way to go about the synthesis for this reaction?


Toluene ---> m-fluorotoluene (or 3-fluorotoluene, or 1-Fluoro-3-methylbenzene)


Thanks in advance.

Title: Re: Toluene to m-fluorotoluene (or 3-Fluortoluene) Synthesis
Post by: MissPhosgene on May 03, 2010, 01:07:20 AM

1. Oxidize (Jones) to acid then make ester (MeI, K2Co3)

2. N,N'-difluoro-1,4-diazobicyclo[2.2.2]octane ditriflate in HCO2H

  or  1-fluoropyridinium tetrafluoroborate or the triflate

3. Reduce, reduce....

or you could just buy it from aldrich.

Title: Re: Toluene to m-fluorotoluene (or 3-Fluortoluene) Synthesis
Post by: MissPhosgene on May 03, 2010, 01:15:24 AM

HPF6 might be better fluorinating agent with the ester. Sorry. My mistake.

Title: Re: Toluene to m-fluorotoluene (or 3-Fluortoluene) Synthesis
Post by: MissPhosgene on May 03, 2010, 01:19:25 AM

HPF6 is a pain though because you have to go through the amine. Easier to go through oxidation and reduction without the additional amine formation step.

Title: Re: Toluene to m-fluorotoluene (or 3-Fluortoluene) Synthesis
Post by: MichaelWestin on May 03, 2010, 12:51:07 PM

Thank you very much  :)