November 23, 2024, 08:00:14 AM
Forum Rules: Read This Before Posting


« previous next »
Pages: [1]   Go Down

Topic: Toluene to m-fluorotoluene (or 3-Fluortoluene) Synthesis  (Read 4779 times)

0 Members and 1 Guest are viewing this topic.

Offline MichaelWestin

  • New Member
  • **
  • Posts: 6
  • Mole Snacks: +0/-0
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.
Logged

Offline MissPhosgene

  • Chemist
  • Full Member
  • *
  • Posts: 364
  • Mole Snacks: +23/-5
  • Gender: Female
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.
Logged
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline MissPhosgene

  • Chemist
  • Full Member
  • *
  • Posts: 364
  • Mole Snacks: +23/-5
  • Gender: Female
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.
Logged
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline MissPhosgene

  • Chemist
  • Full Member
  • *
  • Posts: 364
  • Mole Snacks: +23/-5
  • Gender: Female
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.
Logged
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline MichaelWestin

  • New Member
  • **
  • Posts: 6
  • Mole Snacks: +0/-0
Re: Toluene to m-fluorotoluene (or 3-Fluortoluene) Synthesis
« Reply #4 on: May 03, 2010, 12:51:07 PM »
Thank you very much  :)
Logged
Pages: [1]   Go Up
« previous next »
Sponsored Links