[AlphaScent]

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!

[wildfyr]

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?

[AlphaScent]

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)

[hollytara]

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.