Attempted a sandmeyer reaction today of a 1-bromo-2-amino arene. Don't appear to have any of the product, but all the starting material was consumed. The compound I obtained doesn't have an amine present, but has one more proton present, ie it isnt a 1,2 dihalo compound. It doesnt match with reference spectra for the 2-bromo or chloro. Has anyone seen electrophilic aromatic substitution of a bromo for a chloro under sandmeyer conditions, ie the 1-chloro product. Should be able to get a high res mass spec tomorrow, but would like an idea what to look for.