I am looking for a way to purify an alkyl halide from a pyridine solution. I started with 0.02 grams of pyrene 1-methanol and added to it 20 mL pyrene and 200 uL of SOCl2 at room temperature hoping that the substitution reaction would happen. The solution has been sitting for a day at room temperature as I am figuring out how to recover the pyrene 1-methylchloride (?). The only method that I think of after reading is to let all the solvent evaporate and be left with the pyrene. I'm not well versed in separation techniques (not a chemist); does anyone have better suggestions? Ultimately, I'm looking to modify the pyrene 1-methanol to be a thiol. After making the pyrene 1-methylchloride I was thinking about using thiolurea (with what solvent I don't know) to complete the modification. Does this method seem feasible? What are some considerations that I need to be aware of? Thanks for your input.