Well I tried brominating o-nitrophenol with just liquid bromine and acetic acid. I heated the solution, filtered, washed with H2O and finally recrsytallized with ethanol.
The M.P initially of o-nitrophenol was 45ish and the final product had 66-67 C. The reactant was actually an unknown compound that I had to identify spectroscopically and either derive brominated product or benzoate. I obviously chose the easier one
So the reaction was 2-nitrophenol + Br2 (liquid)
Vogel had the derivative down as a dibrominated compound 2,4-dibromo-6-nitrophenol. I got 2-bromo-6-nitrophenol. March's explained that Bromination of a phenol would lead to ortho being preferable. I might have read it wrong but my product exclusively was a brominated substituent that was ortho to the hydroxyl (i.e. the 2-bromo-6-nitrophenol).
I would have thought that the said product would be a minor simply due to steric hindrance (the Br is huge as hell, it would probably be more hindered next to OH than a simple H in para confirmation).
So I beg to ask the question, why did I get ortho instead of para?
I tried ACS, RCA, Science-direct, SDBS and loads to textbooks, I cannot find IR for 2-bromo-6-nitrophenol anywhere to compare it with my IR. I particularly need help here.
Now the expected product from Vogels would never have occured in the conditions I did my experiment in. The ring would have been far too deactivated for a second bromination to occur, especially in the relatively mild conditions I did it in.
a very lazy chemist.