[AlphaScent]

I synthesized 1-bromo-but-3-ene-2-ol from 1,3-butadiene using NBS in Ether and water.  I prepared the product in 62% yield.  My boss and I were talking, and though about a reaction of bromine in water/THF solvent system due to the miscibility of THF and water.  I don't have access to papers or synthetic procedures.  Does anyone know a good procedure or paper I could read for a synthesis of 1-bromo-but-3-ene-2-ol form a bromine/water system?

Thank you in advance!! 

[Dan]

62% is OK, the starting materials are very cheap. You can do this in a biphasic water/ether system with NBS (81% yield) as detailed here:

http://pubs.acs.org/doi/abs/10.1021/jo01050a068

There is a paper here in which they prepare it using NaBrO₃/NaHSO₃ (in situ BrOH):

http://pubs.acs.org/doi/abs/10.1021/jo00098a012