Just to give everyone an update. I managed to sort out all my bromosafrole extracts. Final yield was approx 41g (0.169moles). Their was a large amount of loses, due to solution flying out of beaker when stirring, being spilled on the floor, excess volumes of solvents etc.. Newbie mistakes. On adding a small portion to conc. H2SO4, the bromo sat as a layer on top and no interaction was noted.
Anyways to 41grams of bromosafrole their was added 32.6 grams (0.219 moles) of NaI in approx 120ml Acetone, roughly 1.3 equiv. This solution was stirred for 40 minutes at room temperature before being poured into a sep funnel. dH2O was added until 2 distinct layers formed as in "First Iodo Separation.jpg below.
The top organic layer was separated and the water layer was subsequently extracted with 3x50ml DCM.
The iodosafrole had a distinctly different smell and colour to the bromosafrole. It was still a very dark solution, but when it had a dark greenish-yellow tint when swirled on the sides of the beaker.
I have all my gassing apparatus/suckback trap made now , just waiting for all the water to boil off from my methylamine solution made by the interaction of Hexamine with HCl.
Hopefully this works out!
