Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: AlphaScent on July 12, 2019, 03:36:00 PM
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Why is the reaction of PBr3 with DMF, producing the Vilsmeier complex, not more widely used as a brominating reagent?
I have done two brominations of primary alcohols and both reactions gave >90% yield and the work up could not be easier.
Is it simply the use of PBr3? This is just a discussion really about this methodology. Has anyone else done this reaction?
Cheers!
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I was under the impression that this is a common way to convert alcohols to bromides.
I have done this reaction. What other methods do you feel are more common for this direct conversion?
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I guess I do not really see it in the literature that often. I feel like I see Appel (Br2/PPh3) a lot more often. Also Finkelstein I feel like is used much more often (MEsylate/Tosylate reacted with NaBr in acetone)
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Straight up HBr works too - if it is primary alcohol not usually any issues since no sterepochemistry or SN1/rearrangement issues.
If you want gentle, CBr4 and PPh3.