A bromination of 2C-H was attempted as described in
https://www.thevespiary.org/rhodium/Rhodium/chemistry/2cb.bromination.html
.
The reaction was run at 1/10th scale of that described in the aforementioned document.
The 2C-H was prepared by Zn/HCOOH reduction of 1-(2,5-dimethoxyphenyl)-2-nitroethane. This reduction was incomplete, leaving some of the starting material in the reaction product. To solve this, the reaction product was washed with 10% NaOH, which resulted in the yellow colour of the contaminated organic product disappearing as the sodium salt of the nitro compound was formed, drawing it out of the organic layer. The organic product was extracted with ether, dried with MgSO4 and evaporated to leave 2C-H as an almost white (v. slight brown tinge) oil that was rubbery smelling.
The bromination reaction was run as described in the document linked above. The reaction certainly created a significant amount of HBr, that fumed in air if the foil lid was left off the container (also ate through the tinfoil).
One day later no crystals have formed, in spite of putting the finished reaction in the fridge (not even any crystals of GAA).
Can anyone enlighten me as to possible reasons this reaction has not run as described?
Has anyone else had a similar experience?
What should be done with the post-reaction mixture. Is it possible to isolate any product do you think?
What work-up would you suggest?
Many thanks for your help.