[PoetryInMotion]

A substitution rxn with tosylated (R)-butan-2-ol with NaI would probably not work since iodide ions are excellent leaving groups. The initially formed (S)-2-iodobutane would therefore be more reactive than the tosylated alcohol and subsequent substitutions would take place and we would get a racemic mixture as a result.

Are there any better methods aviable? Or is the best choise to stick with the racemate and try to separate it (and maybe racemize the (R)-2-iodobutane again and do another separation tp increase the yield)?

[kriggy]

I would try the substitution of tosylate. It should be simple and might work, by adjusting reaction conditions, you might get no further substitution

[critzz]

How about the Appel reaction? R-OH + PPh₃ + I₂ + imidazole  R-I
Or R-OH + PPh₃ + CI₄  R-I
It also inverts the stereocenter.

[PoetryInMotion]

Thank you both of you! I will take a look at the alternative reactions.

I would try the substitution of tosylate. It should be simple and might work, by adjusting reaction conditions, you might get no further substitution

Are there any certain conditions that you would try? Maybe we somehow can make use of the fact that the ioidated product has different solubility properties than the tosylate?