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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: boronic on February 07, 2008, 10:03:34 AM

Title: 2-iodofluorene synthesis
Post by: boronic on February 07, 2008, 10:03:34 AM

Hi. I want to synthesize 2-iodofluorene, using iodination reaction of fluorene. I used procedure described in Organic Letters 2001 vol 3 no 13 2005-2007p but unlucky.:( Please help.

Title: Re: 2-iodofluorene synthesis
Post by: russellm72 on February 07, 2008, 10:45:19 AM

Hi,

I have read the reaction and it seems a simple precipitation...

What exactly did you isolate?

R

Title: Re: 2-iodofluorene synthesis
Post by: boronic on February 08, 2008, 01:55:46 AM

Yes, but i dont get precipitate. And TLC control shows only starting material. The reaction mixture is still dark red. I raised temperature to 100oC but still nothing. Maybe the reason cut be periodic acid. Iodine i got from Aldrich.

 

Title: Re: 2-iodofluorene synthesis
Post by: alphahydroxy on February 08, 2008, 07:53:15 AM

Just a thought, but have you got the right periodic acid? In the paper they use the orthoperiodic acid (H₅IO₆) - could you maybe be using the meta- form ? (HIO₄).

Not sure of the difference in reactivity between the two forms would be, but presumably there is some difference...