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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Knopfleri on May 23, 2019, 08:55:02 AM

Title: Finkelstein reaction: 3-chloro-1-phenyl-1-propanol to 3-iodo-1-phenyl-1-propanol
Post by: Knopfleri on May 23, 2019, 08:55:02 AM

I'm currently working on a project involving the synthesis of Prozac. The second step requires me to substitute the Cl in 3-chloro-1-phenyl-1-propanol with I to form 3-iodo-1-phenyl-1-propanol. I know the way to do this is a Finkelstein reaction with NaI and acetone, since NaI is soluble in acetone whereas NaCl isn't, which shifts the equilibrium to the right, forming R-I.

What I don't know, is how to setup a step-by-step protocol for this reaction, and also the purification and characterization.

The things I'm struggling most with are the concentrations of the acetone and NaI, the temperature at which the reactions works best and how to purify the solution.

For the temperature I read something online about the reflux temperature, but I have no clue how this works.

Purification might be possible with extraction, but again I am clueless as to how.

I can't find step-by-step protocols for Finkelstein reactions, which make it even harder to setup my own

Title: Re: Finkelstein reaction: 3-chloro-1-phenyl-1-propanol to 3-iodo-1-phenyl-1-propanol
Post by: wildfyr on May 23, 2019, 02:51:24 PM

I saw you post this on reddit and feel like you got about the same degree of information you'll find here.

https://www.reddit.com/r/OrganicChemistry/comments/bs2goi/finkelstein_reaction_rcl_to_ri/. Seems like you're good to go.