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Topic: Toluene to m-fluorotoluene (or 3-Fluortoluene) Synthesis  (Read 4400 times)

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Offline MichaelWestin

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Toluene to m-fluorotoluene (or 3-Fluortoluene) Synthesis
« 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.
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Offline MissPhosgene

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Re: Toluene to m-fluorotoluene (or 3-Fluortoluene) Synthesis
« Reply #1 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.
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Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline MissPhosgene

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Re: Toluene to m-fluorotoluene (or 3-Fluortoluene) Synthesis
« Reply #2 on: May 03, 2010, 01:15:24 AM »
HPF6 might be better fluorinating agent with the ester. Sorry. My mistake.
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Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline MissPhosgene

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Re: Toluene to m-fluorotoluene (or 3-Fluortoluene) Synthesis
« Reply #3 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.
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Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline MichaelWestin

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Re: Toluene to m-fluorotoluene (or 3-Fluortoluene) Synthesis
« Reply #4 on: May 03, 2010, 12:51:07 PM »
Thank you very much  :)
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