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Hello,

I would appreciate your help with a bromination reaction. I am trying to brominate 2-aminobenzothiazole; I am expecting ortho-para substitution, with the para position on the benzene ring being the major product.

I dissolve the SM in chloroform, and then at zero degrees, I add 1 equivalent of Bromine. The colour disappears after some time and I know that all of the bromine has reacted. My problem is the next step in the reaction, because SM still appears on the tlc. On my last attempt, I added one more equivalent and after leaving the reaction 12 hours, a yellow precipitate had formed which I filtered off. This yellow solid is barely soluble in chloroform, unlike the SM and shows 2 spots on the tlc. One having the same rf as the SM, the other higher up.

Can anyone give me some pointers as to what Iapos;m doing wrong? Itapos;s supposed to be a simple bromination reaction

Thanks in advance :)

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